Advertisement

Fluorinated Furans and Benzofurans

  • Alexander V. Butin
  • Igor V. Trushkov
  • Olga V. Serdyuk
  • Vladimir T. Abaev
Chapter

Abstract

Synthesis, reactions, and application of furans and benzofurans bearing a fluorine atom and a trifluoromethyl group are reviewed.

Keywords

Fluorofurans Trifluoromethylfurans 

References

  1. 1.
    Liddle J, Allen MJ, Borthwick AD, Brooks DP, Davies DE, Edwards RM, Exall AM, Hamlett C, Irving WR, Mason AM, McCafferty GP, Nerozzi F, Peace S, Philp J, Pollard D, Pullen MA, Shabbir SS, Sollis SL, Westfall TD, Woollard PM, Wu C, Hickey DMB (2008) The discovery of GSK221149A: a potent and selective oxytocin antagonist. Bioorg Med Chem Lett 18:90–94CrossRefGoogle Scholar
  2. 2.
    Cantrell AS, Engelhardt P, Högberg M, Jaskunas RS, Johansson NG, Jordan CL, Kangasmetsä J, Kinnick MD, Lind P, Morin JM, Muesing MA, Noreen R, Öberg B, Pranc P, Sahlberg C, Ternansky RJ, Vasileff RT, Vrang L, West SJ, Zhang H (1996) Phenethylthiazolylthiourea (PETT) compounds as a new class of HIV-1 reverse transcriptase Inhibitors. 2. Synthesis and further structure-activity relationship studies of PETT analogues. J Med Chem 39:4261–4274CrossRefGoogle Scholar
  3. 3.
    Bendale P, Olepu S, Suryadevara PK, Bulbule V, Rivas K, Nallan L, Smart B, Yokoyama K, Ankala S, Pendyala PR, Floyd D, Lombardo LJ, Williams DK, Buckner FS, Chakrabarti D, Verlinde CLMJ, Van Voorhis WC, Gelb MH (2007) Second generation tetrahydroquinoline-based protein farnesyltransferase inhibitors as antimalarials. J Med Chem 50:4585–4605CrossRefGoogle Scholar
  4. 4.
    Shi S, Zhu S, Gerritz SW, Esposito K, Padmanabha R, Li W, Herbst JJ, Wong H, Shu YZ, Lam KS, Sofia MJ (2005) Solid-phase synthesis and anti-infective activity of a combinatorial library based on the natural product anisomycin. Bioorg Med Chem Lett 15:4151–4154CrossRefGoogle Scholar
  5. 5.
    Kuhl A, Svenstrup N, Ladel C, Otteneder M, Binas A, Schiffer G, Brands M, Lampe T, Ziegelbauer K, Rübsamen-Waigmann H, Haebich D, Ehlert K (2005) Biological characterization of novel inhibitors of the gram-positive DNA polymerase IIIC enzyme. Antimicrob Agents Chemother 49:987–995CrossRefGoogle Scholar
  6. 6.
    Jenkins TJ, Guan B, Dai M, Li G, Lightburn TE, Huang S, Freeze BS, Burdi DF, Jacutin-Porte S, Bennett R, Chen W, Minor C, Ghosh S, Blackburn C, Gigstad KM, Jones M, Kolbeck R, Yin W, Smith S, Cardillo D, Ocain TD, Harriman GC (2007) J Med Chem 50:566–584CrossRefGoogle Scholar
  7. 7.
    Hevener KE, Mehboob S, Su P-C, Truong K, Boci T, Deng J, Ghassemi M, Cook JL, Johnson ME (2011) Discovery of a novel and potent class of F. Tularensis enoyl-reductase (fabl) inhibitors by molecular shape and electrostatic matching. J Med Chem 55:268–279CrossRefGoogle Scholar
  8. 8.
    Yun W, Ahmad M, Chen Y, Gillespie P, Conde-Knape K, Kazmer S, Li S, Qian Y, Taub R, Wertheimer SJ, Whittard T, Bolin D (2011) Discovery and optimization of 2-phenyloxazole derivatives as diacylglycerol acyltransferase-1 inhibitors. Bioorg Med Chem Lett 21:7205–7209CrossRefGoogle Scholar
  9. 9.
    Elworthy TR, Kertesz DJ, Kim W, Roepel MG, Quattrocchio-Setti L, Smith DB, Tracy JL, Chow A, Li F, Brill ER, Lach LK, McGee D, Yang DS, Chiou S-S (2004) Lactams as EP4 prostanoid receptor subtype selective agonists. Part 1: 2-pyrrolidinones – stereo-chemical and lower side-chain optimization. Bioorg Med Chem Lett 14:1655–1659CrossRefGoogle Scholar
  10. 10.
    Elworthy TR, Brill ER, Caires CC, Lim W, Lach LK, Tracy JL, Chiou S-S (2005) Lactams as prostanoid receptor ligands. Part 4: 2-piperidones as selective EP4 receptor agonists. Bioorg Med Chem Lett 15:2523–2526CrossRefGoogle Scholar
  11. 11.
    Hutinec A, Rupcic R, Ziher D, Smith KS, Milhous W, Ellis W, Ohrt C, Ivezic Schönfeld Z (2011) An automated, polymer-assisted strategy for the preparation of urea and thiourea derivatives of 15-membered azalides as potential antimalarial chemotherapeutics. Bioorg Med Chem 19:1692–1701CrossRefGoogle Scholar
  12. 12.
    Gammill RB, Bell FP, Bell LT, Bisaha SN, Wilson GJ (1990) Antiatherosclerotic agents. A structurally novel bivalent inhibitor of AcylCoA: cholesterol O-acyltransferase with systemic activity. J Med Chem 33:2685–2687CrossRefGoogle Scholar
  13. 13.
    Serdyuk O, Butin A, Abaev V (2010) Synthesis of fluorofurans and perfluoroalkylfurans. J Fluor Chem 131:296–319CrossRefGoogle Scholar
  14. 14.
    Cerichelli G, Crestoni ME, Fornarini S (1990) The fluorination of five-membered heteroaromatic compounds with elemental fluorine. Gazz Chim Ital 120:749–755Google Scholar
  15. 15.
    Blank SJ, Stephens CE (2006) Oxidative ring opening of 2,5-diarylfurans by selectfluor®. Tetrahedron Lett 47:6849–6850CrossRefGoogle Scholar
  16. 16.
    Burdon J, Tatlow JC, Thomas DF (1966) Tetrafluorofuran. Chem Commun 48–49. doi: 10.1039/C19660000048
  17. 17.
    Burdon J, Chivers GE, Mooney EF, Tatlow JC (1969) Partial fluorination of tetrahydrofuran with cobalt trifluoride. J Chem Soc (C) 1739–1746Google Scholar
  18. 18.
    Burdon J, Chivers GE, Tatlow JC (1970) Highly fluorinated heterocycles. Part III. The preparation and reactions of some polyfluorofurans. J Chem Soc (C) 2146–2151Google Scholar
  19. 19.
    Bailey J, Plevey RG, Tatlow JC (1975) Hexafluorobenzo[b]furan. Tetrahedron Lett 16:869–870CrossRefGoogle Scholar
  20. 20.
    Barton DHR, Hesse RH, Jackman GP, Pechet MM (1977) Fluorination of benzofuran and of N-acylindoles with trifluorofluorooxymethane. J Chem Soc Perkin Trans 1:2604–2608CrossRefGoogle Scholar
  21. 21.
    Perugini R, Ruzziconi R, Sebastiani GV (1983) Synthesis of 2,3-dihalogeno-2,3-dihydrobenzofurans: regioselectivity and stereochemistry. Gazz Chim Ital 113:149–152Google Scholar
  22. 22.
    Nash SA, Gammill RB (1987) The synthesis of 2- and 3-fluorokhellin. Tetrahedron Lett 28:4003–4006CrossRefGoogle Scholar
  23. 23.
    Baciocchi E, Ruzziconi R, Sebastiani GV (1983) Anti and syn eliminations from 2,3-dihalo-2,3-dihydrobenzofurans. The role of the substrate structure and the base-solvent system on the reaction mechanism. J Am Chem Soc 105:6114–6120CrossRefGoogle Scholar
  24. 24.
    Dvornikova E, Bechcicka M, Kamenska-Trela K, Krowczynski A (2003) Synthesis and NMR studies of 2- and 3-fluorosubstituted five-membered heterocycles. J Fluor Chem 124:159–168CrossRefGoogle Scholar
  25. 25.
    Li P, Chai Z, Zhao G, Zhu S-Z (2008) Synthesis of 3-fluoro-2,5-disubstituted furans and further derivative reactions to access fluorine-containing 3,3′-bifurans and tetrasubstituted furans. Synlett 2547–2551Google Scholar
  26. 26.
    Yamada S, Gavryushin A, Knochel P (2010) Convenient electrophilic fluorination of functionalized aryl and heteroaryl magnesium reagents. Angew Chem Int Ed 49:2215–2218CrossRefGoogle Scholar
  27. 27.
    Yamada S, Knochel P (2010) Large-scale preparation of aromatic fluorides via electrophilic fluorination with functionalized aryl- or heteroarylmagnesium reagents. Synthesis 2490–2494Google Scholar
  28. 28.
    Forrest AK, O’Hanlon PJ (1995) The preparation and lithiation of bromofluorofurans via a novel fluorodecarboxylation. Tetrahedron Lett 36:2117–2118CrossRefGoogle Scholar
  29. 29.
    Song R, Lin W, Jiang Q (2011) A convenient synthesis of 5-fluorofuran-2-carboxylic acid. Tetrahedron Lett 52:4965–4966CrossRefGoogle Scholar
  30. 30.
    Martin-Santamaria S, Carroll MA, Carroll CM, Carter CD, Pike VW, Rzepa HS, Widdowson DA (2000) Fluoridation of heteroaromatic iodonium salts – experimental evidence supporting theoretical prediction of the selectivity of the process. Chem Commun 649–650Google Scholar
  31. 31.
    Ichikawa J, Wada Y, Fujiwara M, Sakoda K (2002) The nucleophilic 5-endo-trig cyclization of 1,1-difluoro-1-alkenes: ring-fluorinated hetero- and carbocycle synthesis and remarkable effect of the vinylic fluorines on the disfavored process. Synthesis 1917–1936Google Scholar
  32. 32.
    Ichikawa J, Wada Y, Okauchi T, Minami T (1997) 5-endo-trigonal cyclization of o-substituted gem-difluorostyrenes: syntheses of 2-fluorinated indoles, benzo[b]furans and benzo[b]thiophenes. Chem Commun 1537–1538Google Scholar
  33. 33.
    Sham HL, Betebenner DA (1991) A new and concise synthesis of 3-fluoro-2,5-disubstituted furans. J Chem Soc Chem Commun 1134–1135Google Scholar
  34. 34.
    Arimitsu S, Hammond GB (2007) Selective synthesis of fluorinated furan derivatives via AgNO3-catalyzed activation of an electronically deficient triple bond. J Org Chem 72:8559–8561CrossRefGoogle Scholar
  35. 35.
    Arimitsu S, Jacobsen JM, Hammond GB (2008) Synthesis of 2,4,5-trisubstituted 3-fluorofurans via sequential iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols. J Org Chem 73:2886–2889CrossRefGoogle Scholar
  36. 36.
    Li Y, Wheeler KA, Dembinski R (2011) Electrophilic cyclizations of 2-fluoroalk-3-yn-1-ones: room-temperature synthesis of diversely 2,5-disubstituted 3,4-fluorohalofurans. Eur J Org Chem 2767–2771Google Scholar
  37. 37.
    Li Y, Wheeler KA, Dembinski R (2012) Room temperature syntheses of entirely diverse substituted β-fluorofurans. Org Biomol Chem 10:2395–2408CrossRefGoogle Scholar
  38. 38.
    Li Y, Wheeler KA, Dembinski R (2010) Gold(I)-catalyzed cycloisomerization of 2-fluoroalk-3-yn-1-ones: synthesis of 2,5-substituted 3-fluorofurans. Adv Synth Catal 352:2761–2766CrossRefGoogle Scholar
  39. 39.
    Lie MSF, Jie K, Lau MML, Lam CNW (2003) Synthesis of novel tri- and tetrasubstituted C18 furan fatty esters. Lipids 38:1293–1297CrossRefGoogle Scholar
  40. 40.
    Moon HR, Kim HO, Jeong LS (2002) Synthesis of 2′,3′-didehydro-2′,3′-dideoxy-2′-flu-oro apionucleosides as potential antiviral agents. J Chem Soc Perkin Trans 1:1800–1804CrossRefGoogle Scholar
  41. 41.
    Lee K, Zhou W, Kelley LLC, Momany C, Chu CK (2002) Synthesis of unsaturated fluoride containing D- and L-pyranosyl nucleosides. Tetrahedron Asymmetry 13:1589–1598CrossRefGoogle Scholar
  42. 42.
    Derenberg M, Hodge P (1971) Reaction of difluorocarbene with 2-benzylidenecyclohexanones to afford phenylfluorofurans. Chem Commun 233–234Google Scholar
  43. 43.
    Xu W, Chen Q-Y (2003) A novel approach of cycloaddition of difluorocarbene to α, β-unsaturated aldehydes and ketones: synthesis of gem-difluorocyclopropyl ketones and 2-fluorofurans. Org Biomol Chem 1:1151–1156CrossRefGoogle Scholar
  44. 44.
    Xu W, Dolbier WR, Salazar J (2008) Ionic liquid, surrogate hydrogen bromide reagent for ring opening of cyclopropyl ketones. J Org Chem 73:3535–3538CrossRefGoogle Scholar
  45. 45.
    Wang H, Gu W, Zhang G, Huan Z, Chen J-P (1999) Revisiting the reactions of halocarbenes with tetraphenylcyclone. J Chem Res (M) 1501–1509Google Scholar
  46. 46.
    Paleta O, Volkov A, Hetflejs J (2000) Fluorinated butanolides and butenolides, part 5. Synthesis and nucleophilic reactions of 3-chloro-2-fluoro-2-buten-4-olide as tetronic acid analogue. Conjugate addition of hard nucleophiles and vinylic halogen displacement with soft phosphorus nucleophiles. J Fluor Chem 102:147–157CrossRefGoogle Scholar
  47. 47.
    Pomeisl K, Cejka J, Kvicala J, Paleta O (2007) Synthesis of 3-fluorofuran-2(H)-ones based on Z/E photoisomerisation and cyclisation of 2-fluoro-4-hydroxybut-2-enoates. Eur J Org Chem 5917–5925Google Scholar
  48. 48.
    Pomeisl K, Kvicala J, Paleta O (2006) Convenient synthesis of 3-fluoro-4,5-diphenylfuran-2(5H)-one from benzoin ethers. Novel and efficient Z-E isomerisation and cyclisation of 2-fluoroalkenoate precursors, substitution of vinylic fluorine. J Fluor Chem 127:1390–1397CrossRefGoogle Scholar
  49. 49.
    Girard Y, Atkinson JG, Belanger PC, Fuentes JJ, Rokach J, Rooney CS, Remy DC, Hunt CA (1983) Synthesis, chemistry, and photochemical substitutions of 6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-ones. J Org Chem 48:3220–3234CrossRefGoogle Scholar
  50. 50.
    Naumann D, Kischkewitz J (1990) Trifluormethylierubgsreaktionen von CF3I, Te(CF3)2, Sb(CF3)3, Hg(CF3)2, und Cd(CF3)2⋅D mit furan, thiophen, pyrrol und p-benzochinon. J Fluor Chem 46:265–281CrossRefGoogle Scholar
  51. 51.
    Kino T, Nagase Y, Ohtsuka Y, Yamamoto K, Uraguchi D, Tokuhisa K, Yamakawa T (2010) Trifluoromethylation of various aromatic compounds by CF3I in the presence of Fe(II) compound, H2O2 and dimethylsulfoxide. J Fluor Chem 131:98–105CrossRefGoogle Scholar
  52. 52.
    Iqbak N, Choi S, Ko E, Cho EJ (2012) Trifluoromethylation of heterocycles via visible light photoredox catalysis. Tetrahedron Lett 53:2005–2008CrossRefGoogle Scholar
  53. 53.
    Sawada H, Nakayama M, Yoshida M, Yoshida T, Kamigata N (1990) Trifluoromethylation of aromatic compounds with bis(trifluoroacetyl) peroxide. J Fluor Chem 46:423–431CrossRefGoogle Scholar
  54. 54.
    Popkov SV, Kuzenkov AV (2005) Synthesis of trifluoromethyl-substituted heteroaroma-tic aldehydes. Russ Chem Bull 54:1672–1674 (Izv Akad Nauk, Ser Khim 1623–1625)CrossRefGoogle Scholar
  55. 55.
    Kobayashi Y, Kumadaki I, Hanzawa Y (1977) Studies on organic fluorine compounds. XXII. Synthesis and reactions of (trifluoromethyl)benzofurans. Chem Pharm Bull 25:3009–3012CrossRefGoogle Scholar
  56. 56.
    Kobayashi Y, Kumadaki I (1980) Studies on organic fluorine compounds. Part 27. Abnormal reactions in the trifluoromethylation of aromatic compounds with trifluoromethyl iodide and copper powder. J Chem Soc Perkin Trans 1:661–664CrossRefGoogle Scholar
  57. 57.
    Ye Y, Sanford MS (2012) Merging visible-light photocatalysis and transition-metal catalysis in the copper-catalyzed trifluoromethylation of boronic acids with CF3I. J Am Chem Soc 134:9034–9037CrossRefGoogle Scholar
  58. 58.
    Ye Y, Künzi SA, Sanford MS (2012) Practical method for the Cu-mediated trifluoromethylation of arylboronic acids with CF3 radical derived from NaSO2CF3 and tert-butyl hydroperoxide (TDHP). Org Lett 14:4979–4981CrossRefGoogle Scholar
  59. 59.
    Chu L, Qing F-L (2010) Copper-mediated oxidative trifluoromethylation of boronic acids. Org Lett 12:5060–5063CrossRefGoogle Scholar
  60. 60.
    Zhang C-P, Cai J, Zhou C-B, Wang X-P, Zheng X, Gu Y-C, Xiao J-C (2011) Copper-mediated trifluoromethylation of arylboronic acids by trifluoromethyl sulfonium salts. Chem Commun 47:9516–9518Google Scholar
  61. 61.
    Liu T, Shen Q (2011) Copper-catalyzed trifluoromethylation of aryl and vinyl boronic acids with an electrophilic trifluoromethylating reagent. Org Lett 13:2342–2345CrossRefGoogle Scholar
  62. 62.
    Liu T, Shao X, Wu Y, Shen Q (2012) Highly selective trifluoromethylation of 1,3-disubstituted arenes through iridium-catalyzed arene borylation. Angew Chem Int Ed 51:540–543CrossRefGoogle Scholar
  63. 63.
    Ye Y, Lee SH, Sanford MS (2011) Silver-mediated trifluoromethylation of arenes using TMSCF3. Org Lett 13:5464–5467CrossRefGoogle Scholar
  64. 64.
    Nishida M, Fujii S, Aoki T, Hayakawa Y, Muramatsu H, Morita T (1990) Synthesis and polymerization of ethynylthiophenes and ethynylfurans containing trifluoromethyl groups. J Fluor Chem 46:445–459CrossRefGoogle Scholar
  65. 65.
    Grigorash RV, Lyalin VV, Alekseeva LA, Yagupol’skii LM (1977) 5-Trifluoromethyl-furan derivatives. Chem Heterocycl Comp 13:1280–1282 (Khim Geterotsikl Soed 1607–1609)CrossRefGoogle Scholar
  66. 66.
    Lyalin VV, Grigorash RV, Alekseeva LA, Yagupolskii LM (1975) Fluorination of furantetracarboxylic acid by sulfur tetrafluoride. Russ J Org Chem 11:456–457 (Zh Org Khim 11:460–461)Google Scholar
  67. 67.
    Lyalin VV, Grigorash RV, Alekseeva LA, Yagupolskii LM (1975) Mono(trifluoromethyl)furans and bis(trifluoromethyl)furans. Russ J Org Chem 11:1073–1077, Zh Org Khim 11:1086–1090Google Scholar
  68. 68.
    Yagupolskii LM, Vechirko EP, Kondratenko NV, Liepinsh EE, Shpaer EG, Zhuk RA (1981) Synthesis of 2-trifluoromethyltetrahydrofuran and 2-perfluoro-tert-butyltetrahydrofuran and their pyrimidinenucleoside analogs. Russ J Org Chem 17:167–170 (Zh Org Khim 17:186–191)Google Scholar
  69. 69.
    Lyalin VV, Grigorash RV, Alekseeva LA, Yagupolskii LM (1984) Reaction of 3,4-furandicarboxylic acid derivatives with sulfur tetrafluoride in a hydrogen fluoride medium. Russ J Org Chem 20:769–772 (Zh Org Khim 20:846–849)Google Scholar
  70. 70.
    Nowak I, Dmowski W, Manko WA (1995) Unusual reaction of sulphur tetrafluoride: conversion of the methyl group into difluoromethyl and trifluoromethyl groups. J Fluor Chem 75:115–116CrossRefGoogle Scholar
  71. 71.
    Sherman WR, Freifelder M, Stone GR (1960) Three 2-fluoroalkyl-5-nitrofurans. J Org Chem 25:2048–2049CrossRefGoogle Scholar
  72. 72.
    Weis CD (1962) A diene-retrodiene-diene reaction. The synthesis of 2,3,5,6-tetrakis-(trifluoromethyl)-7-oxabicyclo[2.2.1]-2,5-heptadiene. J Org Chem 27:3693–3695CrossRefGoogle Scholar
  73. 73.
    Jiang B, Zhang F, Xiong W (2002) The regio- and stereoselective addition of carbon nucleophiles to trifluoromethyl phenylsulfanyl acetylene: a novel and expeditious approach to 3-trifluoromethyl furans. Tetrahedron Lett 43:665–667CrossRefGoogle Scholar
  74. 74.
    Abubakar AB, Booth BL, Tipping AE (1991) Reaction of 2-lithio-3,4-bis(trifluoromethyl)furan with electrophiles. J Fluor Chem 55:189–198CrossRefGoogle Scholar
  75. 75.
    Abubakar AB, Booth BL, Suliman NNE, Tipping AE (1992) Some reactions of 3,4-bis(trifluoromethyl)furan and its precursor, 2,3-bis(trifluoromethyl)-7-oxabicyclo[2.2.1]-hepta-2,5-diene: novel isocoumarin formation from thermal reaction of the furan with ethyl propionate. J Flu Chem 56:359–371CrossRefGoogle Scholar
  76. 76.
    Wilson WS, Warrener RN (1972) A mild retro-[π4S+π2S] cleavage route to furans and fulvenes. J Chem Soc Chem Commun 211–212Google Scholar
  77. 77.
    Chambers RD, Roche AJ, Rock MH (1996) Polyhalogenated heterocyclic compounds. Part 41. Cycloaddition reactions involving hexafluorobut-2-yne and 1,1,1,2,4,4,4-heptafluorobut-2-ene. J Chem Soc Perkin Trans 1:1095–1100CrossRefGoogle Scholar
  78. 78.
    Barlow MG, Suliman NNE, Tipping AE (1995) A high-yield synthesis of 3-carboethoxy-4-trifluoromethylfuran and some Diels-Alder reactions of this furoate with acetylenic dienophiles. J Fluor Chem 70:59–69CrossRefGoogle Scholar
  79. 79.
    Nezis A, Fayn J, Cambon A (1991) Obtention de 3-F-alkyl-4-ethoxycarbonyl furanes. J Fluor Chem 53:297–299CrossRefGoogle Scholar
  80. 80.
    Nezis A, Fayn J, Cambon A (1991) Synthese d’heterocycles F-alkyles par reaction de Diels-Alder sur les F-alkyl propynoates. J Fluor Chem 53:285–295CrossRefGoogle Scholar
  81. 81.
    Warrener RN, Wang J-M, Weerasuria KDV, Russell RA (1990) Transfer technology III: the synthesis of bridged cyclic polyenes using a new retrosynthetic algorithm as a guide. Tetrahedron Lett 31:7069–7072CrossRefGoogle Scholar
  82. 82.
    Thalhammer F, Wallfahrer U, Sauer J (1988) 1,3,4-Oxadiazole als heterocyclische 4π-komponenten in Diels-Alder-reaktionen. Tetrahedron Lett 29:3231–3234CrossRefGoogle Scholar
  83. 83.
    Seitz G, Gerninghaus C (1994) Cycloadditions of 1,3,4-oxadiazoles. Pharmazie 49:102–106Google Scholar
  84. 84.
    Kawada K, Kitagawa O, Kobayashi Y (1985) Studies on organic fluorine compounds. XLV. Synthesis and regioselective substitution reaction of 3-trifluoromethylfuran. Chem Pharm Bull 33:3670–3674CrossRefGoogle Scholar
  85. 85.
    Kobatake T, Yoshida S, Yorimitsu H, Oshima K (2010) Reaction of 2-(2,2,2-trifluoroethylidene)-1,3-dithiane 1-oxide with ketones under Pummerer conditions and its application to the synthesis of 3-trifluoromethyl-substituted five-membered heteroarenes. Angew Chem Ed 49:2340–2343CrossRefGoogle Scholar
  86. 86.
    Bambury RE, Yaktin HK, Wyckoff KK (1968) Trifluoromethylfurans. J Heterocycl Chem 5:95–100CrossRefGoogle Scholar
  87. 87.
    Smith JO, Mandal BK, Filler R, Beery JW (1997) Reaction of ethyl 4,4,4-trifluoroacetate enolate with 3-bromo-1,1,1-trifluoroacetone: synthesis of 2,4-bis(trifluoromethyl)furan. J Fluor Chem 81:123–128CrossRefGoogle Scholar
  88. 88.
    Bambury RE, Miller LF (1970) Trifluoromethylfurans. II. J Heterocycl Chem 7:269–273CrossRefGoogle Scholar
  89. 89.
    Gibson CL, Paulini K, Suckling CJ (1997) Synthesis of potential inhibitors of GTP-cyclohydrolase I: an efficient synthesis of 8-substituted 7-deazaguanines. Chem Commun 371–372Google Scholar
  90. 90.
    Gibson CL, Ohta K, Paulini K, Suckling CJ (1997) Specific inhibitors in vitamin biosynthesis. Part 10. Synthesis of 7- and 8-substituted 7-deazaguanines. J Chem Soc Perkin Trans 1:3025–3031Google Scholar
  91. 91.
    Mosslemin MH, Yavari I, Anary-Abbasinejad M, Nateghi MR (2004) Reaction between tert-butyl isocyanide and 1,1,1-trifluoro-4-aryl-butane-2,4-diones. Synthesis of new trifluoromethylated furan derivatives. J Fluor Chem 125:1497–1500CrossRefGoogle Scholar
  92. 92.
    Nishida M, Hayakawa Y, Matsui M, Shibata K, Muramatsu H (1991) Synthesis of 2,5-diethyl-3,4-bis(trifluoromethyl)furan and its derivatives. J Heterocycl Chem 28:225–229CrossRefGoogle Scholar
  93. 93.
    Linderman RJ, Jamois EA, Tennyson SD (1994) Synthesis of and analysis of thiol additions to β-alkyl-α, β-unsaturated trifluoromethyl ketones. J Org Chem 59:957–962CrossRefGoogle Scholar
  94. 94.
    Zhang D, Yuan C (2007) Reaction of 1,2-unsaturated trifluoromethyl ketones and their conversion to 1-(trifluoromethyl)furan derivatives. Eur J Org Chem 3916–3924Google Scholar
  95. 95.
    Zhang J, Zhao X, Li Y, Lu L (2006) Highly efficient synthesis of 4-trifluoromethylfuran derivatives via a sequential deprotection-annulation reaction. Tetrahedron Lett 47:4737–4739CrossRefGoogle Scholar
  96. 96.
    Usachev BI (2011) First nucleophilic addition of acetylide to 1,3-diketonate anions: reaction of 1-aryl-4,4,4-trifluorobutane-1,3-diones with sodium acetylide. Tetrahedron Lett 52:6726–6728CrossRefGoogle Scholar
  97. 97.
    Chambers RD, Kirk JR, Powell RL (1983) Polyhalogenoheterocyclic compounds. Part 35. Reactions of fluorinated alkenes and cycloalkenes with enolate anions. J Chem Soc Perkin Trans 1:1239–1242CrossRefGoogle Scholar
  98. 98.
    Kuroboshi M, Shinozaki T, Ishihara T, Ando T (1987) A convenient synthesis of fluorine-containing highly-substituted furans through new fluoride ion-catalyzed reaction of 1-alkyl-F-1-alkenyl phosphates. Chem Lett 1621–1622Google Scholar
  99. 99.
    Briscoe MW, Chambers RD, Mullins, SJ, Nakamura T, Drakesmith FG (1990) A synthesis of novel perfluorodienes. J Chem Soc Chem Commun 1127–1128Google Scholar
  100. 100.
    Briscoe MW, Chambers RD, Mullins SJ, Nakamura T, Vaughan JFS (1994) Reactions involving fluoride ion. Part 39. Reactions of perfluorinated dienes with oxygen and sulphur nucleophiles. J Chem Soc Perkin Trans 1:3119–3124CrossRefGoogle Scholar
  101. 101.
    Chambers RD, Vaughan JFS, Mullins SJ, Nakamura T, Roche AJ (1995) Fluorinated dienes. J Fluor Chem 72:231–233CrossRefGoogle Scholar
  102. 102.
    Burger K, Helmreich B (1992) Ein neues Verfahren zur positionsselektiven Einführung von Trifluormethylgruppen in Heteroaromaten: Synthese von 3-Trifluormethylfuran. J Prakt Chem 334:311–316CrossRefGoogle Scholar
  103. 103.
    Burger K, Helmreich B (1992) Synthesis of 3-trifluoromethylfurans from β,β-bis(trifluoromethyl) α,β-unsaturated ketones and tin(II) chloride. J Chem Soc Chem Commun 348–349Google Scholar
  104. 104.
    Burger K, Helmreich B, Hennig L, Spengler J, Albericio F, Fuchs A (2007) Partially fluorinated heterocycles from 4,4-bis(trifluoromethyl)-hetero-1,3-dienes via C–F bond activation – synthesis of 2-fluoro-3-(trifluoromethyl)furans. Monatsh Chem 138:227–236CrossRefGoogle Scholar
  105. 105.
    Chambers RD, Lindley AA, Fielding HC (1978) Photochemical transformations of perfluoro-tri- and -tetra-methylfurans. J Fluor Chem 12:337–340CrossRefGoogle Scholar
  106. 106.
    Chambers RD, Lindley AA, Philpot PD, Fielding HC, Hutchinson J, Whittaker G (1978) Perfluorinated derivatives of furan via novel cyclisation reactions of perfluoro-olefins. J Chem Soc Chem Commun 431–432Google Scholar
  107. 107.
    Chambers RD, Lindley AA, Philpot PD, Fielding HC, Hutchinson J, Whittaker G (1979) Reactions involving fluoride ion. Part 16. Nucleophilic attack on a perfluorotetraalkylethylene and a synthesis of perfluorotetramethylfuran. J Chem Soc Perkin Trans 1:214–219CrossRefGoogle Scholar
  108. 108.
    Briscoe MW, Chambers RD, Mullins SJ, Nakamura T, Vaughan JFS, Drakesmith FG (1994) Reactions involving fluoride ion. Part 38. New fluorinated dienes by defluorination. J Chem Soc Perkin Trans 1:3115–3118CrossRefGoogle Scholar
  109. 109.
    Bartlett S, Chambers RD, Kelly NM (1980) A novel furan synthesis. Tetrahedron Lett 21:1891–1892CrossRefGoogle Scholar
  110. 110.
    Jullien J, Pechine JM, Perez F, Piade JJ (1982) Flash vacuum thermolysis of β-keto-trimethylsilyl-enol-ethers. Synthesis of allenic and furanic derivatives. Tetrahedron 38:1413–1416CrossRefGoogle Scholar
  111. 111.
    Khlebnikova TS, Isakova VG, Lakhvich FA (2009) Reaction of 2-perfluoroalkanoyl-сyclohexane-1,3-diones with diazomethane. Russ J Org Chem 45:519–522 (Zh Org Khim 45:534–537)CrossRefGoogle Scholar
  112. 112.
    Bouillon J-P, Henin B, Huot J-F, Portella C (2002) 1,1-Bis(ethylsulfanyl)perfluorobut-1-ene as starting material for the synthesis of substituted 2-trifluoromethylfurans and –pyrroles. Eur J Org Chem 1556–1561Google Scholar
  113. 113.
    Bouillon J-P, Kikelj V, Tinant B, Harakat D, Porterlla C (2006) Synthesis of new trifluoromethylated furans, dihydrofurans and butenolides starting from γ-ketothioesters and diisopropylamine. Synthesis 1050–1056Google Scholar
  114. 114.
    Hess U, König WA (1981) Synthese von Furanderivaten aus N-Methylaminosäuren. Liebigs Ann Chem 1606–1609Google Scholar
  115. 115.
    Denisenko AV, Tverdokhlebov AV, Tolmachev AA, Volovenko YM, Shishkina SV, Shishkin OV (2010) Synthesis of masked 2-amino-3-furancarboxaldehydes. Synthesis 1009–1013Google Scholar
  116. 116.
    Begue J-P, Bonnet-Delpon D, Dogbeavou R, Ourevitch M (1993) Trifluoromethylated furans via iodocyclisation of γ-unsaturated ethyl trifluoroacetates. J Chem Soc Perkin Trans 1:2787–2791CrossRefGoogle Scholar
  117. 117.
    Zakharova VM, Nikolaev VA (2007) Rhodium(II)-catalyzed intramolecular reactions of methyl 4-diazo-5-oxo-3-trifluoromethylalk-2-enoates in the presence of 2,5-dimethylfuran. Russ J Org Chem 43:930–932 (Zh Org Khim 43:931–933)CrossRefGoogle Scholar
  118. 118.
    Yoneda N, Matsuoka S, Miyaura N, Fukuhara T, Suzuki A (1990) Preparation of 1-aryl- or 1-alkenyl-2-(perfluoroalkyl)acetylenes. Bull Chem Soc Jpn 63:2124–2126CrossRefGoogle Scholar
  119. 119.
    Zhou H, Niu J-J, Xu J-W, Hu S-J (2009) Novel route to 2-trifluoromethylated benzofurans. Synth Commun 39:716–732CrossRefGoogle Scholar
  120. 120.
    Jiang Z-X, Qing F-L (2003) Sodium carbonate as carbon dioxide source for the synthesis of cyclic carbonates containing the trifluoromethyl group. J Fluor Chem 123:57–60CrossRefGoogle Scholar
  121. 121.
    Konno T, Chae J, Ishihara T, Yamanaka H (2004) A first regioselective synthesis of 3-fluoroalkylated benzofurans via palladium-catalyzed annulation of fluorine-containing internal alkynes with variously substituted 2-iodophenol. Tetrahedron 60:11695–11700CrossRefGoogle Scholar
  122. 122.
    Kobatake T, Fujino D, Yoshida S, Yorimitsu H, Oshima K (2010) Synthesis of 3-trifluoromethylbenzo[b]furans from phenols via direct ortho functionalization by extended Pummerer reaction. J Am Chem Soc 132:11838–11840CrossRefGoogle Scholar
  123. 123.
    Kaltenbronn JS, Quin J, Reisdorph BR, Klutchko S, Reynolds EE, Welch KM, Flynn MA, Doherty AM (1997) Benzofuran derivatives as ETA-selective, non-peptide endothelin antagonists. Eur J Med Chem 32:425–431CrossRefGoogle Scholar
  124. 124.
    Judd DB, Dowle MD, Middlemiss D, Scopes DIC, Ross BC, Jack TI, Pass M, Tranquillini E, Hobson JE, Panchal TA, Stuart PG, Paton JMS, Hubbard T, Hilditch A, Drew GM, Robertson MJ, Clark KL, Travers A, Hunt AAE, Eddershaw PJ, Bayliss MK, Manchee GR, Donnelly MD, Walker DG, Richards SA (1994) Bromobenzofuran-based non-peptide antagonists of angiotensin II: GR138950, a potent antihypertensive agent with high oral bioavailability. J Med Chem 37:3108–3120CrossRefGoogle Scholar
  125. 125.
    Kuckländer U, Herweg-Wahl U, Poll W, Rickerich L (1988) Darstellung und Eigenschaften von fluorierten Benzofuran-Derivaten. Chem Ber 121:1841–1845CrossRefGoogle Scholar
  126. 126.
    Davydov DV, Beletskaya IP (2004) Synthesis of naphtho[2,3-b]furan-4,9-diones having a trifluoromethyl group under conditions of phase-transfer catalysis. Russ J Org Chem 40:134–136 (Zh Org Khim 40:143–145)CrossRefGoogle Scholar
  127. 127.
    Onys’ko PP, Proklina NV, Prokopenko VP, Gololobov YG (1987) Intramolecular substitution of o-nitro group in 2,6-dinitrobenzene derivatives. Russ J Org Chem 23:549–552 (Zh Org Khim 23:606–610)Google Scholar
  128. 128.
    Kuckländer U (1983) Zur Umsetzung eines cyclishen Halbaminals mit CH-aciden Verbindungen. Arch Pharm 316:449–453CrossRefGoogle Scholar
  129. 129.
    Gallos JK, Lianis PS, Nicolaides DN (1989) Reactions of furazano[3,4-b]quinoxalines with phosphorus ylides and an unusual oxidative transformation of the transylidation product. J Heterocycl Chem 26:1415–1420CrossRefGoogle Scholar
  130. 130.
    Wang Y, Zhu S (2001) A simple synthesis of fluoroalkyl substituted dihydrofurans by rhodium(II)-catalyzed 1,3-dipolar reactions. Tetrahedron 57:3383–3387CrossRefGoogle Scholar
  131. 131.
    Pang W, Zhu S, Xin Y, Jiang H, Zhu S (2010) Rh2(OAc)4 catalyzed formation of fluorine-containing polysubstituted furans from diazocompounds and aromatic alkynes. Tetrahedron 66:1261–1266CrossRefGoogle Scholar
  132. 132.
    Akhani RK, Atiq-ur-Rehman, Schnatter WFK (2009) Incorporation of hexafluorobutyne into furans or phenols via reaction with iron(0) carbine or vinylketene complexes. Tetrahedron Lett 50:930–932CrossRefGoogle Scholar
  133. 133.
    Wang Y, Luo Y-C, Hu X-Q, Xu P-F (2011) A powerful cascade approach for expeditious synthesis of trifluoromethylated furans. Org Lett 13:5346–5349CrossRefGoogle Scholar
  134. 134.
    Ochiai K, Takita S, Eiraku T, Kojima A, Iwase K, Kishi T, Fukuchi K, Yasue T, Adams DR, Allcock RW, Jiang Z, Kohno Y (2012) Phosphodiesterase inhibitors. Part 3: design, synthesis and structure-activity relationships of dual PDE3/4-inhibitory fused bicyclic heteroaromatic-dihydropyridazinones with anti-inflammatory and bronchodilatory activity. Bioorg Med Chem 20:1644–1658CrossRefGoogle Scholar
  135. 135.
    Lee C-J, Jang Y-J, Wu Z-Z, Lin W (2012) Preparation of functional phosphorus zwitterions from activated alkanes, aldehydes, and tributylphosphine: synthesis of polysubstituted furo[3,2-c]coumarins. Org Lett 14:1906–1909CrossRefGoogle Scholar
  136. 136.
    Morandi B, Carreira EM (2011) Expedient preparation of trifluoromethyl-substituted benzofuranols. Org Lett 13:5984–5985CrossRefGoogle Scholar
  137. 137.
    Rudenko AP, Aristov SA, Vasil’ev AV (2004) Oxidative heterocyclization of 4-(4-methoxy-3-fluorophenyl)-1,1,1-trifluorobut-3-yn-2-one in a system CF3CO2H-CH2Cl2-PbO2. Russ J Org Chem 40:1221 (Zh Org Khim 40:1268)CrossRefGoogle Scholar
  138. 138.
    Aristov SA, Vasil’ev AV, Rudenko AP (2006) Oxidation of aromatic compounds: XIV. Oxidation of arylethynyl ketones in the system CF3CO2H-CH2Cl2-PbO2. Russ J Org Chem 42:66–72 (Zh Org Khim 42:74–80)CrossRefGoogle Scholar
  139. 139.
    Kobayashi Y, Hanzawa Y, Nakanishi Y, Kashiwagi T (1978) Conversion of a valence-bond isomer of hexakis(trifluoromethyl)oxepin to tetrakis(trifluoromethyl)furan. Tetrahedron Lett 19:1019–1022CrossRefGoogle Scholar
  140. 140.
    Boriack CJ, Laganis ED, Lemal DM (1978) Perfluorotetramethylfuran. Tetrahedron Lett 19:1015–1018CrossRefGoogle Scholar
  141. 141.
    Tyvorskii VI, Pukin AV, Bobrov DN (2001) Condensation of stereoisomeric 2-acetyl-2,3-diphenyloxiranes with ethyl trifluoroacetate. Chem Heterocycl Comp 37:540–545 (Khin Geterotsikl Soed 592–597)CrossRefGoogle Scholar
  142. 142.
    Kawada K, Kitagawa O, Taguchi T, Hanzawa Y, Kobayashi Y, Iitaka Y (1985) Studies on organic fluorine compounds. XLVII. Synthesis of trifluoromethylated sugars through the aldol reaction of 2-trimethylsilyloxy-4-trifluoromethylfuran. Chem Pharm Bull 33:4216–4222CrossRefGoogle Scholar
  143. 143.
    Okano T, Ueda T, Ito K, Kodaira K, Hosokawa K, Muramatsu H (1986) Synthesis of so-me ethynyltrifluoromethylfurans and their polymerization. J Fluor Chem 31:451–459CrossRefGoogle Scholar
  144. 144.
    Grigorash RV, Lyalin VV, Alekseeva LA, Yagupolskii LM (1978) Tetrakis(trifluoro-methyl)furan. Russ J Org Chem 14:2414–2415 (Zh Org Khim 14:2623–2624)Google Scholar
  145. 145.
    Burger K, Fuchs A, Hennig L, Helmreich B (2001) Low temperature domino reaction. A ready access to trifluoromethyl substituted butenolides and their thioanalogues. Tetrahedron Lett 42:1657–1659CrossRefGoogle Scholar
  146. 146.
    Burger K, Hennig L, Fuchs A, Greif D, Spengler J, Albericio F (2005) Domino reactions with fluorinated five-membered heterocycles – syntheses of trifluoromethyl substituted butenolides and γ-ketoacids. Monatsh Chem 136:1763–1779CrossRefGoogle Scholar
  147. 147.
    Burger K, Fuchs A, Hennig L, Helmreich B, Greif D (2001) Domino reactions with 2-fluoro-3-trifluoromethylfurans and –thiophenes. Monatsh Chem 132:929–945CrossRefGoogle Scholar
  148. 148.
    Bouillon J-P, Tinant B, Nuzillard J-M, Porterlla C (2004) Synthesis of new 3-(1-ethylsulfanyl-2-perfluoroalkyl)-5-hydroxy-5-methyl (or 5-phenyl)-1,5-dihydro-pyrrol-2-ones starting from γ-keto thioesters and amines. Synthesis 711–721Google Scholar
  149. 149.
    Kobayashi Y, Hanzawa Y (1978) Reaction of tetrakis(trifluoromethyl)furan and its photo-adduct. Tetrahedron Lett 19:4301–4302CrossRefGoogle Scholar
  150. 150.
    Nishida M, Hayakawa Y, Matsui M, Shibata K, Muramatsu H (1992) Synthesis and photochemical reaction of 1,4-dialkyl-7-oxa-2,3,5,6-tetrakis(trifluoromethyl)bicyclo-hepta-2,5-diene. J Heterocycl Chem 29:113–116CrossRefGoogle Scholar
  151. 151.
    Abubakar AB, Booth BL, Tipping AE (1990) Novel Diels-Alder cycloaddition involving two α, β-unsaturated esters in the formation of isocoumarins from the reaction of ethyl propynoate with 3,4-bis(trifluoromethyl)furan. J Fluor Chem 47:353–359CrossRefGoogle Scholar
  152. 152.
    Li P, Gu J-W, Ying Y, He Y-M, Zhang H-f, Zhao G, Zhu S-Z (2010) Palladium-catalyzed alkenylation of fluoro-substituted furans via C-H activation to form tetrasubstituted furans. Tetrahedron 66:8387–8391CrossRefGoogle Scholar
  153. 153.
    Li P, Chai Z, Zhao G, Zhu S-Z (2009) Pd-catalyzed direct arylation of 3-fluorofurans utilizing the neighboring effect of fluorine atom: facile synthesis of tetrasubstituted monofluorofurans. Tetrahedron 65:1673–1678CrossRefGoogle Scholar
  154. 154.
    Baxendale IR, Schou SC, Sedelmeier J, Ley SV (2010) Multi-step synthesis by using modular flow reactors: the preparation of yne-ones and their use in heterocyclic synthesis. Chem Eur J 16:89–94CrossRefGoogle Scholar
  155. 155.
    Yoshida M, Imai R, Komatsu Y, Morinaga Y, Kamigata N, Iyoda M (1993) Convenient preparations and Michael reactions of 4-fluoroalkylated but-2-en-4-olides. J Chem Soc Perkin Trans 1:501–504CrossRefGoogle Scholar
  156. 156.
    Yanai H, Takahashi A, Taguchi T (2010) 1,4-Addition of silicon dienoates to α,β-unsaturated aldehydes catalyzed by in situ-generated silicon Lewis acid. Chem Commun 46:8728–8730Google Scholar
  157. 157.
    Kastron VV, Dubur GY, Vitolin’ RO, Kimenis AA (1979) Synthesis and pharmacological activity of 4-furyl-1,4-dihydropyridines. Pharm Chem J 13:611–616 (Khim-Farm Zh, 13, N6:57–62)Google Scholar
  158. 158.
    Wagner J, Vitali P, Schoun J, Giroux E (1977) Metal complexation by α-mercapto-β-aryl acrylic acids. Can J Chem 55:4028–4036CrossRefGoogle Scholar
  159. 159.
    Muramatsu H, Okumura A, Shibata K, Matsui M (1994) Synthesis, absorption spectra, and photostability of triarylmethane dye ethynylogues containing trifluoromethyl group(s). Chem Ber 127:1627–1632CrossRefGoogle Scholar
  160. 160.
    Baumann M, Baxendale IR, Ley SV, Nikbin N, Smith CD, Tierney JP (2008) A modular flow reactor for performing Curtius rearrangements as a continuous flow process. Org Biomol Chem 6:1577–1586CrossRefGoogle Scholar
  161. 161.
    Patch RJ, Brandt BM, Asgari D, Baindur N, Chadha NK, Georgiadis T, Cheung WS, Petrounia IP, Donatelli RR, Chaikin MA, Player MR (2007) Potent 2′-aminoanilide inhibitors of cFMS as potential anti-inflammatory agents. Bioorg Med Chem Lett 17:6070–6074CrossRefGoogle Scholar
  162. 162.
    Shin Y, Chen W, Habel J, Duckett D, Ling YY, Koenig M, He Y, Vojkovsky T, LoGrasso P, Kamenecka TM (2009) Synthesis and SAR of piperazine amides as novel c-jun N-terminal kinase (JNK) inhibitors. Bioorg Med Chem Lett 19:3344–3347CrossRefGoogle Scholar
  163. 163.
    Mazurov AA, Miao L, Bhatti BS, Strachan J-P, Akireddy S, Murthy S, Kombo D, Xiao Y, Hammond P, Zhang J, Hauser TA, Jordan KG, Miller CH, Speake JD, Gatto GJ, Yohannes D (2012) Discovery of 3-(5-chloro-2-furoyl)-3,7-diazabicyclo[3.3.0]octane (TC-6683, AZD1446), a novel highly selective α4β2 nicotinic acetylcholine receptor agonist for the treatment of cognitive disorders. J Med Chem 55:9181–9194CrossRefGoogle Scholar
  164. 164.
    Ashton WT, Chang LL, Flanagan KL, Hutchins SM, Naylor EM, Chakravarty PK, Patchett AA, Greenlee WJ, Chen T-B, Faust KA, Chang RSL, Lotti VJ, Zingaro GJ, Schorn TW, Siegl PKS, Kivlighn SD (1994) Triazolinone biphenylsulfonamide derivatives as orally active angiotensin II antagonists with potent AT1 receptor affinity and enhanced AT2 affinity. J Med Chem 37:2808–2824CrossRefGoogle Scholar
  165. 165.
    Heightman TD, Gaster LM, Pardoe SL, Pilleux J-P, Hadley MS, Middlemiss DN, Price GW, Roberts C, Scott CM, Watson JM, Gordon LJ, Holland VA, Powles J, Riley GJ, Stean TO, Trail BK, Upton N, Austin NE, Ayrton AD, Coleman T, Cutler L (2005) 8-Piperazinyl-2,3-dihydropyrrolo[3,2-g]isoquinolines: potent, selective, orally bioavailable 5-HT1 receptor ligands. Bioorg Med Chem Lett 15:4370–4374CrossRefGoogle Scholar
  166. 166.
    Sandham DA, Barker L, Beattie D, Beer D, Bidlake L, Bentley D, Butler KD, Craig S, Farr D, Ffoulkes-Jones C, Fozard JR, Haberthuer S, Howes C, Hynx D, Jeffers S, Keller TH, Kirkham PA, Maas JC, Mazzoni L, Nicholls A, Pilgrim GE, Schaebulin E, Spooner GM, Stringer R, Tranter P, Turner KL, Tweed MF, Walker C, Watson SJ, Cuenoud BM (2004) Synthesis and biological properties of novel glucocorticoid androstene C-17 furoate esters. Bioorg Med Chem 12:5213–5224CrossRefGoogle Scholar
  167. 167.
    Snyder DS, Tradtrantip L, Yao C, Kurth MJ, Verkman AS (2011) Potent, metabolically stable benzopyrimido-pyrrolo-oxazine-dione (BPO) CFTR inhibitors for polycystic kidney disease. J Med Chem 54:5468–5477CrossRefGoogle Scholar
  168. 168.
    Lockman JW, Reeder MD, Suzuki K, Ostanin K, Hoff R, Bhoite L, Austin H, Baichwal V, Willardsen JA (2010) Inhibition of eEF-2K by thieno[2,3-b]pyridine analogues. Bioorg Med Chem Lett 20:2283–2286CrossRefGoogle Scholar
  169. 169.
    Bulbule VJ, Rivas K, Verlinde CLMJ, Van Voorhis WC, Gelb MH (2008) 2-Oxotetrahydroquinoline-based antimalarials with high potency and metabolic stability. J Med Chem 51:384–387CrossRefGoogle Scholar
  170. 170.
    Zuercher WJ, Buckholz RG, Campobasso N, Collins JL, Galardi CM, Gampe RT, Hyatt SM, Merrihew SL, Moore JT, Oplinger JA, Reid PR, Spearing PK, Stanley TB, Stewart EL, Wilson TM (2010) Discovery of tertiary sulfonamides as potent liver X receptor antagonists. J Med Chem 53:3412–3416CrossRefGoogle Scholar
  171. 171.
    Yu Y, Dwyer MP, Chao J, Aki C, Chao J, Purakkattle B, Rindgen D, Bond R, Mayer-Ezel R, Jakway J, Qiu H, Hipkin RW, Fossetta J, Gonsiorek W, Bian H, Fan X, Terminelli C, Fine J, Lundell D, Merritt JR, He Z, Lai G, Wu M, Taveras A (2008) Synthesis and structure-activity relationships of heteroaryl substituted-3,4-diamino-3-cyclobut-3-ene-1,2-dione CXCR2/CXCR1 receptor antagonists. Bioorg Med Chem Lett 18:1318–1322CrossRefGoogle Scholar
  172. 172.
    Jamieson C, Maclean JKF, Brown CI, Campbell RA, Gillen KJ, Gillespie J, Kazemier B, Kiczun M, Lamont Y, Lyons AJ, Moir EM, Morrow JA, Pantling J, Rankovic Z, Smith L (2011) Structure based evolution of a novel series of positive modulators of the AMPA receptor. Bioorg Med Chem Lett 21:805–811CrossRefGoogle Scholar

Copyright information

© Springer International Publishing Switzerland 2014

Authors and Affiliations

  • Alexander V. Butin
    • 1
  • Igor V. Trushkov
    • 2
  • Olga V. Serdyuk
    • 3
  • Vladimir T. Abaev
    • 4
  1. 1.Department of ChemistryPerm State UniversityPermRussian Federation
  2. 2.Department of ChemistryM. V. Lomonosov Moscow State UniversityMoscowRussian Federation
  3. 3.Department of Chemistry and Pharmacy, Chair of Organic Chemistry IUniversity of Erlangen-NurembergErlangenGermany
  4. 4.Department of ChemistryNorth-Ossetian State UniversityVladikavkazRussian Federation

Personalised recommendations