Abstract
A new phosphine-catalyzed [3+2] annulation reaction between activated 1,4-naphthoquinones and acetylenecarboxylates is described. This reaction provides a facile and efficient route to a variety of biologically promising and novel naphtho[1,2-\(b\)]furans. This devised method provides a first example for the synthesis of diverse naphtho[1,2-\(b\)]furan derivatives from 1,4-naphthoquinones via phosphine-catalyzed [3+2] annulation.
Graphical Abstract
A variety of novel naphtho[1,2-\(b\)]furans were synthesized via the phosphine-catalyzed [3+2] annulation of activated 1,4-naphthoquinones and electron-deficient acetylenecarboxylates. In some reactions, both furannulation adducts and reductive/nucleophilic conjugate addition products were produced.
Similar content being viewed by others
References
Kwiecień H, Śmist M, Kowalewska M (2012) Recent development on the synthesis of benzo[\(b\)]- and naphtho[\(b\)]furans: a review. Curr Org Synth 9:529–560. doi: 10.2174/157017912802651393
Sastry MNV, Claessens S, Habonimana P, De Kimpe N (2010) Synthesis of the natural products 3-hydroxymollugin and 3-methoxymollugin. J Org Chem 75:2274–2280. doi:10.1021/jo100024b
Lumb J-P, Choong KC, Trauner D (2008) Ortho-quinone methides from para-quinones: total synthesis of rubioncolin B. J Am Chem Soc 130:9230–9231. doi:10.1021/ja803498r
Srivastava V, Negi AS, Kumar JK, Faridi U, Sisodia BS, Darokar MP, Luqman S, Khanuja SPS (2006) Synthesis of 1-(3’,4’,5’-trimethoxy)phenylnaphtho[2,1-\(b\)]furan as a novel anticancer agent. Bioorg Med Chem Lett 16:911–914. doi: 10.1016/j.bmcl.2005.10.105
Ho L-K, Don M-J, Chen H-C, Yeh S-F, Chen J-M (1996) Inhibition of hepatitis B surface antigen secretion on human hepatoma cells. Components from Rubia cordifolia. J Nat Prod 59:330–333. doi:10.1021/NP960200H
Le Guével R, Oger F, Lecorgne A, Dudasova Z, Chevance S, Bondon A, Barath P, Simonneaux G, Salbert G (2009) Identification of small molecule regulators of the nuclear receptor HNF4\(\alpha \) based on naphthofuran scaffolds. Bioorg Med Chem 17:7021–7030. doi: 10.1016/j.bmc.2009.07.079
Hendrix M, Boess F-G, Erb C, Flessner T, Van Kampen M, Luithle J, Methfessel C, Wiese WB (2003) Preparation of 2-heteroarylcarboxylic acid amides for therapeutic use as nicotinic acetylcholine receptor agonists. WO 2003055878:A1
Ikeura Y, Yoshida M, Sugiyama H (2006) Preparation of fused furan derivatives as \(\text{ IKK }\beta \) inhibitors. WO 2006036031 A1
Paal M, Ruehter G, Schotten T (2000) Preparation of imidazoline derivatives for the treatment of diabetes, especially type II diabetes. WO 2000078726 A1
Tseng C-H, Lin C-S, Shih P-K, Tsao L-T, Wang J-P, Cheng C-M, Tzeng C-C, Chen Y-L (2009) Furo[3’,2’:3,4]naphtho[1,2-\(d\)]imidazole derivatives as potential inhibitors of inflammatory factors in sepsis. Bioorg Med Chem 17:6773–6779. doi: 10.1016/j.bmc.2009.07.054
Abd El-Wahab AHF, Al-Fifi ZIA, Bedair AH, Ali FM, Halawa AHA, El-Agrody AM (2011) Synthesis, reactions and biological evaluation of some new naphtho[2,1-\(b\)]furan derivatives bearing a pyrazole nucleus. Molecules 16:307–318. doi: 10.3390/molecules16010307
Prabhakar KR, Veerapur VP, Bansal P, Vipan KP, Reddy KM, Barik A, Reddy BKD, Reddanna P, Priyadarsini KI, Unnikrishnan MK (2006) Identification and evaluation of antioxidant, analgesic/anti-inflammatory activity of the most active ninhydrin-phenol adducts synthesized. Bioorg Med Chem 14:7113–7120. doi:10.1016/j.bmc.2006.06.068
Lumb J-P, Trauner D (2005) Biomimetic synthesis and structure elucidation of rubicordifolin, a cytotoxic natural product from Rubia cordifolia. J Am Chem Soc 127:2870–2871. doi:10.1021/ja042375g
Son JK, Jung SJ, Jung JH, Fang Z, Lee CS, Seo CS, Moon DC, Min BS, Kim MR, Woo MH (2008) Anticancer constituents from the roots of Rubia cordifolia L. Chem Pharm Bull 56:213–216. doi:10.1248/cpb.56.213
Itokawa H, Qiao Y, Takeya K (1991) Anthraquinones, naphthoquinones and naphthohydroquinones from Rubia oncotricha. Phytochemistry 30:637–640. doi:10.1016/0031-9422(91)83742-4
Ishiguro K, Ohira Y, Oku H (1998) Antipruritic dinaphthofuran-7,12-dione derivatives from the pericarp of impatiens balsamina. J Nat Prod 61:1126–1129. doi:10.1021/NP9704718
Kubota F (1990) Electrically conductive polymers from naphthofuran derivatives and their analogs. JP 02075625 A
Muroyama Y, Matsuo M (1974) Furan derivatives. JP 49072262 A
Klymchenko AS, Ozturk T, Pivovarenko VG, Demchenko AP (2001) Synthesis and spectroscopic properties of benzo- and naphthofuryl-3-hydroxychromones. Can J Chem 79:358–363. doi:10.1139/v01-066
Abdul-Aziz M, Auping JV, Meador MA (1995) Synthesis of substituted 2,3,5,6-Tetraarylbenzo[1,2-\(b\):4,5-\(b\)’]difurans. J Org Chem 60:1303–1308. doi: 10.1021/jo00110a038
Frederiksen PK, Jørgensen M, Ogilby PR (2001) Two-photon photosensitized production of singlet oxygen. J Am Chem Soc 123:1215–1221. doi:10.1021/ja003468a
Albota M, Beljonne D, Brédas J-L, Ehrlich JE, Fu J-Y, Heikal AA, Hess SE, Kogej T, Levin MD, Marder SR, McCord-Maughon D, Perry JW, Röckel H, Rumi M, Subramaniam G, Webb WW, Wu X-L, Xu C (1998) Design of organic molecules with large two-photon absorption cross sections. Science 281:1653–1656. doi:10.1126/science.281.5383.1653
Hide F, Díaz-Garzía MA, Schwartz BJ, Heeger AJ (1997) New developments in the photonic applications of conjugated polymers. Acc Chem Res 30:430–436. doi:10.1021/AR950191O
Stranius K, Iashin V, Nikkonen T, Muuronen M, Helaja J, Tkachenko N (2014) Effect of mutual position of electron donor and acceptor on photoinduced electron transfer in supramolecular chlorophyll-fullerene dyads. J Phys Chem A 118:1420–1429. doi:10.1021/jp412442t
Yu Y, Li Y, Qin Z, Jiang R, Liu H, Li Y (2013) Designed synthesis and supramolecular architectures of furan-substituted perylene diimide. J Colloid Interface Sci 399:13–18. doi:10.1016/j.jcis.2013.02.042
Park KK, Jeong J (2005) Facile synthesis of regio-isomeric naphthofurans and benzodifurans. Tetrahedron 61:545–553. doi:10.1016/j.tet.2004.11.022
Arias L, Vara Y, Cossío FP (2012) Regioselective preparation of benzo[\(b\)]furans from phenols and \(\alpha \)-bromoketones. J Org Chem 77:266–275. doi: 10.1021/jo201841y
Anwar S, Huang W-Y, Chen C-H, Cheng Y-S, Chen K (2013) An efficient Friedel-Crafts/ oxa-Michael/aromatic annulation: rapid access to substituted naphtho[2,1-\(b\)]furan, naphtho[1,2-\(b\)]furan, and benzofuran derivatives. Chem Eur J 19:4344–4351. doi: 10.1002/chem.201204221
Brimble MA, Elliott RJ, McEwan JF (2000) Diels–Alder addition of acyclic dienes to chiral naphthoquinones. Aust J Chem 53:571–576
Brimble MA, McEwan JF, Turner P (1998) Asymmetric Michael addition of 2-trimethylsilyloxyfuran to chiral naphthoquinones. Tetrahedron Asymmetry 9:1257–1267. doi:10.1016/S0957-4166(98)00088-3
Brimble MA, Elliott RJR (1997) Addition of siloxydienes to 2-substituted 1,4-benzoquinones and 1,4-naphthoquinones. Tetrahedron 53:7715–7730. doi:10.1016/S0040-4020(97)00436-5
Brimble MA, Burgess C, Halim R, Petersson M, Ray J (2004) Synthesis of pyrrolo[3,2-\(b\)]benzofurans and pyrrolo[3,2-\(b\)]naphthofurans via addition of a silyloxypyrrole to activated quinones. Tetrahedron 60:5751–5758. doi: 10.1016/j.tet.2004.05.008
Brimble MA, Laita O, Robinson JE (2006) Addition of 2- tert-butyldimethylsilyloxythiophene to activated quinones: an approach to thia analogs of kalafungin. Tetrahedron 62:3021–3027. doi:10.1016/j.tet.2006.01.040
Barker D, Brimble MA, Do P, Turner P (2003) Addition of silyloxydienes to 2,6-dibromo-1,4-benzoquinone: an approach to highly oxygenated bromonaphthoquinones for the synthesis of thysanone. Tetrahedron 59:2441–2449. doi:10.1016/S0040-4020(03)00291-6
Mudiganti NVS, Claessens S, De Kimpe N (2009) Ytterbium triflate-catalyzed conjugate addition of \(\beta \)-ketoesters to activated 1,4-naphthoquinones. Tetrahedron 65:1716–1723. doi:10.1016/j.tet.2008.12.021
Xia L, Lee YR (2014) Regioselective synthesis of novel and diverse naphtho[1,2-\(b\)]furan-3-carboxamides and benzofuran-3-carboxamides by cascade formal [3 + 2] cycloaddition. RSC Adv 4:36905–36916. doi: 10.1039/C4RA07862D
Xia L, Lee YR (2013) A novel and efficient synthesis of diverse dihydronaphtho[1,2-\(b\)]furans using the ceric ammonium nitrate-catalyzed formal [3 + 2] cycloaddition of 1,4-naphthoquinones to olefins and its application to furomollugin. Org Biomol Chem 11:6097–6107. doi: 10.1039/c3ob40977e
Sun Y-W, Xu Q, Shi M (2013) Gold-catalyzed reaction of oxabicyclic alkenes with electron-deficient terminal alkynes to produce acrylate derivatives. Beilstein J Org Chem 9:1969–1976. doi:10.3762/bjoc.9.233
Nasiri F, Malakutikhah D (2011) Stereoselective reaction between alkyl propiolates and phenols in the presence of sodium azide in tert-butyl alcohol. Monatshefte fuer Chemie 142:807–812. doi:10.1007/s00706-011-0514-6
Fan M-J, Li G-Q, Li L-H, Yang S-D, Liang Y-M (2006) DABCO-catalyzed reaction of phenols or 1,2-diphenols with activated alkynes leading to the formation of alkenoic acid esters or 1,3-dioxole derivatives. Synthesis 2286–2292. doi:10.1055/s-2006-942437
Wang Z, Liu B, Li Y, Zhao W (2011) Synthesis and bioactivity of novel 1-substituted-1\(H\)-1,2,3-triazole-4-carboxamide. Youji Huaxue 31:317–323
Hoberg H, Riegel HJ (1983) Nickel(II)-induced carbon–carbon linkage between carbon monoxide and alkynes with maintenance of the triple bond. J Organomet Chem 241:245–250. doi:10.1016/S0022-328X(00)98511-5
Düeckert H, Pries V, Khedkar V, Menninger S, Bruss H, Bird AW, Maliga Z, Brockmeyer A, Janning P, Hyman A, Grimme S, Schüermann M, Preut H, Huebel K, Ziegler S, Kumar K, Waldmann H (2012) Natural product-inspired cascade synthesis yields modulators of centrosome integrity. Nat Chem Biol 8:179–184. doi:10.1038/nchembio.758
Baskar B, Wittstein K, Sankar MG, Khedkar V, Schüermann M, Kumar K (2012) Stereoselective cascade double-annulations provide diversely ring-fused tetracyclic benzopyrones. Org Lett 14:5924–5927. doi:10.1021/ol3028412
Düeckert H, Khedkar V, Waldmann H, Kumar K (2011) Lewis base catalyzed [4+2] annulation of electron-deficient chromone-derived heterodienes and acetylenes. Chem Eur J 17:5130–5137. doi:10.1002/chem.201003572
Khedkar V, Liu W, Düeckert H, Kumar K (2010) Efficient and atom-economic synthesis of \(\beta \)-substituted \(\beta \)-chromonyl-\(\alpha ,\beta \)-unsaturated carbonyls through molecular rearrangement. Synlett 403–406. doi:10.1055/s-0029-1219176
Waldmann H, Khedkar V, Düeckert H, Schüermann M, Oppel IM, Kumar K (2008) Asymmetric synthesis of natural product inspired tricyclic benzopyrones by an organocatalyzed annulation reaction. Angew Chem Int Ed 47:6869–6872. doi:10.1002/anie.200802413
Yavari I, Souri S, Sirouspour M, Djahaniani H, Nasiri F (2005) Synthesis of alkyl 3-aryloxypropenoates and alkyl 2-arylacrylates through nucleophilic addition to alkyl propiolates. Synthesis 1761–1764. doi:10.1055/s-2005-865359
Acknowledgments
This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2012R1A1A4A01009620).
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Xia, L., Somai Magar, K.B. & Lee, Y.R. Synthesis of novel and diverse naphtho[1,2-b]furans by phosphine-catalyzed [3+2] annulation of activated 1,4-naphthoquinones and acetylenecarboxylates. Mol Divers 19, 55–66 (2015). https://doi.org/10.1007/s11030-014-9555-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11030-014-9555-1