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Solid-Phase Synthesis of Seven-Membered Heterocycles with Two Nitrogen Atoms

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Solid-Phase Synthesis of Nitrogenous Heterocycles

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 52))

Abstract

Due to the importance of diazepines and diazepanes in medicinal chemistry and chemical biology, their preparation from diverse starting materials has been frequently reported. In this chapter, we summarize all strategies employing the method of solid-phase synthesis. More than seventeen different types of target compounds are accessible. The individual approaches are grouped according to the type of the target scaffold.

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Abbreviations

AA:

Amino acid

Boc:

t-Butyloxycarbonyl

BAL:

Backbone amide linker

BTC:

Bis(trichloromethyl) carbonate

DABCO:

1,4-Diazabicyclo[2.2.2]octane

DBU:

1,8-Diazabicyclo[5.4.0]undec-7-ene

DCC:

N,N′-Dicyclohexylcarbodiimide

DCE:

Dichloroethane

DCM:

Dichloromethane

DIAD:

Diisopropyl azodicarboxylate

DIBAL-H:

Diisobutylaluminium hydride

DIC:

N,N′-Diisopropylcarbodiimide

DIEA:

N,N-Diisopropylethylamine

DEAD:

Diethyl azodicarboxylate

DECP:

Diethyl cyanophosphonate

DMAP:

4-Dimethylaminopyridine

DMF:

N,N-Dimethylformamide

DMSO:

Dimethyl sulfoxide

DMTMM:

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride

EEDQ:

N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline

Fmoc:

Fluorenylmethoxycarbonyl

HATU:

[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate)

HOBt:

1-Hydroxybenzotriazole

MBHA:

Methylbenzhydrylamine

NMP:

N-Methylpyrrolidone

Nos:

Nitrobenzenesulfonyl

TBTU:

N,N,N′,N′-Tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate

TBP:

Tributylphosphine

TEA:

Triethylamine

THF:

Tetrahydrofuran

TFA:

Trifluoroacetic acid

TFMSA:

Trifluoromethanesulfonic acid

TPP:

Triphenylphosphine

References

  1. Charan RD, Schlingmann G, Janso J, Bernan V, Feng X, Carter GTJ (2004) Nat Prod 67(8):1431–1433

    Google Scholar 

  2. Huang RM, Ma W, Dong JD, Zhou XF, Xu T, Lee KJ, Yang X, Xu SH, Liu Y (2010) Molecules 15(2):871–877

    Article  CAS  Google Scholar 

  3. Hadjipavlou-Litina D, Hansch C (1994) Chem Rev 94(6):1483–1505

    Article  CAS  Google Scholar 

  4. Butcher JW, Liverton NJ, Claremon DA, Freidinger RM, Jurkiewicz NK, Lynch JJ, Salata JJ, Wang J, Dieckhaus CM, Slaughter DE, Vyas K (2003) Bioorg Med Chem Lett 13(6):1165–1168

    Article  CAS  Google Scholar 

  5. Haynes SW, Gao X, Tang Y, Walsh CT (2012) J Am Chem Soc 134(42):17444–17447

    Article  CAS  Google Scholar 

  6. Breslin HJ, Kukla MJ, Kromis T, Cullis H, De Knaep F, Pauwels R, Andries K, De Clercq E, Janssen MAC, Janssen PAJ (1999) Bioorg Med Chem 7(11):2427–2436

    Article  CAS  Google Scholar 

  7. Anzini M, Canullo L, Braile C, Cappelli A, Gallelli A, Vomero S, Menziani MC, De Benedetti PG, Rizzo M, Collina S, Azzolina O, Sbacchi M, Ghelardini C, Galeotti N (2003) J Med Chem 46(18):3853–3864

    Article  CAS  Google Scholar 

  8. Chen CY, Lee PH, Lin YY, Yu WT, Hu WP, Hsu CC, Lin YT, Chang LS, Hsiao CT, Wang JJ, Chung MI (2013) Bioorg Med Chem Lett 23(24):6854–6859

    Article  CAS  Google Scholar 

  9. Sandra CM, Cortes Eduardo C, Simon HO, Apan Teresa R, Camacho Antonio N, Lijanova V, Marcos MG (2012) Anti-Cancer Agents Med Chem 12(6):611–618

    Article  CAS  Google Scholar 

  10. Sternbach LH (1979) J Med Chem 22(1):1–7

    Article  CAS  Google Scholar 

  11. Merrifield RB (1963) J Am Chem Soc 85(14):2149–2154

    Article  CAS  Google Scholar 

  12. Kamal A, Reddy KL, Devaiah V, Shankaraiah N, Reddy DR (2006) Mini Rev Med Chem 6(1):53–69

    Article  CAS  Google Scholar 

  13. Kaur N (2013) ChemInform 44(20)

    Google Scholar 

  14. Verma A, Ram Yadav M, Giridhar R, Prajapati N, Tripathi C, Saraf K (2013) Comb Chem High Throughput Screen 16(5):345–393

    Article  CAS  Google Scholar 

  15. Bevacqua F, Basso A, Gitto R, Bradley M, Chimirri A (2001) Tetr Lett 42(43):7683–7685

    Article  CAS  Google Scholar 

  16. Zhu Z, Sun ZY, Ye Y, McKittrick B, Greenlee W, Czarniecki M, Fawzi A, Zhang H, Lachowicz JE (2009) Bioorg Med Chem Lett 19(17):5218–5221

    Article  CAS  Google Scholar 

  17. Combs AP, Saubern S, Rafalski M, Lam PY (1999) Tetr Lett 40(9):1623–1626

    Article  CAS  Google Scholar 

  18. Ou L, Shao Z, Chen W, Giulianotti MA, Houghten RA, Yu Y (2011) Synlett 2011(15):2259–2261

    Article  CAS  Google Scholar 

  19. Pathak R, Roy AK, Kanojiya S, Batra S (2005) Tetr Lett 46(32):5289–5292

    Article  CAS  Google Scholar 

  20. Bunin BA, Ellman JA (1992) J Am Chem Soc 114(27):10997–10998

    Article  CAS  Google Scholar 

  21. Bunin BA, Plunkett MJ, Ellman JA (1994) Proc Natl Acad Sci U S A 91(11):4708–4712

    Article  CAS  Google Scholar 

  22. Plunkett MJ, Ellman JA (1995) J Am Chem Soc 117(11):3306–3307

    Article  CAS  Google Scholar 

  23. Plunkett MJ, Ellman JA (1995) J Org Chem 60(19):6006–6007

    Article  CAS  Google Scholar 

  24. Plunkett MJ, Ellman JA (1997) J Org Chem 62(9):2885–2893

    Article  CAS  Google Scholar 

  25. DeWitt SH, Kiely JS, Stankovic CJ, Schroeder MC, Cody DM, Pavia MR (1993) Proc Natl Acad Sci U S A 90(15):6909–6913

    Article  CAS  Google Scholar 

  26. Dewitt SH, Schroeder MC, Stankovic CJ, Strode JE, Czarnik AW (1994) Drug Develop Res 33(2):116–124

    Article  CAS  Google Scholar 

  27. Lattmann E, Billington DC, Arayarat P, Singh H, Offel M (1999) Sci Asia 25(2):107–112

    Article  CAS  Google Scholar 

  28. Laustsen LS, Sams CK (2007) J Comb Chem 9(6):1094–1103

    Article  CAS  Google Scholar 

  29. Lattmann E, Billington DC, Poyner DR, Arayarat P, Howitt SB, Lawrence S, Offel M (2002) Drug Des Discov 18(1):9–21

    Article  CAS  Google Scholar 

  30. Matsushita K, Okamoto C, Yoshimoto M, Harada K, Kubo M, Fukuyama Y, Hioki H (2010) J Comb Chem 12(3):311–314

    Article  CAS  Google Scholar 

  31. Lee K, Mun SJ, Ha DC, Lee KI, Gong YD, Lee JC (2006) Bull Korean Chem Soc 27(7):974–975

    Article  CAS  Google Scholar 

  32. Boutard N, Dufour-Gallant J, Deaudelin P, Lubell WD (2011) J Org Chem 76(11):4533–4545

    Article  CAS  Google Scholar 

  33. Dufour-Gallant J, Chatenet D, Lubell WD (2015) J Med Chem 58(11):4624–4637

    Article  CAS  Google Scholar 

  34. Bhalay G, Blaney P, Palmer VH, Baxter AD (1997) Tetr Lett 38(48):8375–8378

    Article  CAS  Google Scholar 

  35. Zhang J, Goodloe WP, Lou B, Saneii H (2000) Molec Divers 5(3):127–130

    Article  CAS  Google Scholar 

  36. Wu Z, Ercole F, FitzGerald M, Perera S, Riley P, Campbell R, Pham Y, Rea P, Sandanayake S, Mathieu MN, Bray AM, Ede NJ (2003) J Comb Chem 5(2):166–171

    Article  CAS  Google Scholar 

  37. Hone ND, Wilson W, Reader JC (2003) Tetr Lett 44(46):8493–8495

    Article  CAS  Google Scholar 

  38. Im I, Webb TR, Gong YD, Kim JI, Kim YC (2004) J Comb Chem 6(2):207–213

    Article  CAS  Google Scholar 

  39. Lee JY, Im I, Webb TR, McGrath D, Song MR, Kim YC (2009) Bioorg Chem 37(3):90–95

    Article  CAS  Google Scholar 

  40. Malik L, Kelly NM, Ma JN, Currier EA, Burstein ES, Olsson R (2009) Bioorg Med Chem Lett 19(6):1729–1732

    Article  CAS  Google Scholar 

  41. Ali FE, Yuan CC, Ross ST, Hall LB (2000) Molec Divers 5(1):1–5

    Article  CAS  Google Scholar 

  42. Thurston DE (1993) In: Molecular aspects of anticancer drug-DNA interactions. Springer, pp 54–88

    Google Scholar 

  43. Berry JM, Philip W, Thurston DE (2000) Tetr Lett 41(32):6171–6174

    Article  CAS  Google Scholar 

  44. Kamal A, Reddy GSK, Raghavan S (2001) Bioorg Med Chem Lett 11(3):387–389

    Article  CAS  Google Scholar 

  45. Kamal A, Reddy GSK, Reddy KL (2001) Tetr Lett 42(39):6969–6971

    Article  CAS  Google Scholar 

  46. Kaplánek R, Krchňák V (2013) Tetr Lett 54(21):2600–2603

    Article  CAS  Google Scholar 

  47. Shankaraiah N, Markandeya N, Espinoza-Moraga M, Arancibia C, Kamal A, Santos LS (2009) Synthesis 2009(13):2163–2170

    Article  CAS  Google Scholar 

  48. Kamal A, Reddy GSK, Reddy KL, Raghavan S (2002) Tetr Lett 43(11):2103–2106

    Article  CAS  Google Scholar 

  49. Kamal A, Reddy KL, Devaiah V, Reddy GSK (2003) Tetr Lett 44(25):4741–4745

    Article  CAS  Google Scholar 

  50. Kamal A, Shankaraiah N, Reddy KL, Devaiah V (2006) Tetr Lett 47(25):4253–4257

    Article  CAS  Google Scholar 

  51. Kamal A, Prabhakar S, Shankaraiah N, Markandeya N, Venkat Reddy P, Srinivasulu V, Sathish M (2013) Tetr Lett 54(33):4435–4441

    Article  CAS  Google Scholar 

  52. Kamal A, Reddy KL, Devaiah V, Shankaraiah N, Reddy YN (2004) Tetr Lett 45(41):7667–7669

    Article  CAS  Google Scholar 

  53. Brouillette Y, Verdié P, Martinez J, Lisowski V (2008) Synlett 2008(15):2360–2364

    Article  CAS  Google Scholar 

  54. Ludolph B, Waldmann H (2009) Tetr Lett 50(26):3148–3150

    Article  CAS  Google Scholar 

  55. Kamal A, Reddy KL, Devaiah V, Shankaraiah N, Suresh Kumar Reddy G, Raghavan S (2007) J Comb Chem 9(1):29–42

    Article  CAS  Google Scholar 

  56. Kamal A, Shankaraiah N, Devaiah V, Reddy KL (2006) Tetr Lett 47(37):6553–6556

    Article  CAS  Google Scholar 

  57. Kamal A, Shankaraiah N, Prabhakar S, Reddy C, Markandeya N, Reddy KL, Devaiah V (2008) Bioorg Med Chem Lett 18(7):2434–2439

    Article  CAS  Google Scholar 

  58. Lee SC, Park SB (2007) Chem Commun 36:3714–3716

    Article  CAS  Google Scholar 

  59. Lemrová B, Soural M (2012) ACS Comb Sci 14(12):645–650

    Article  CAS  Google Scholar 

  60. Fülöpová V, Gucký T, Grepl M, Soural M (2012) ACS Comb Sci 14(12):651–656

    Article  CAS  Google Scholar 

  61. Fülöpová V, Krchňák V (2014) ACS Comb Sci 16(8):412–420

    Article  CAS  Google Scholar 

  62. Trapani P, Volná T, Soural M (2016) ACS Comb Sci 18(6):349–354

    Article  CAS  Google Scholar 

  63. Fülöpová V, Funk P, Popa I, McMaster C, Soural M (2015) Eur J Org Chem 2015(16):3551–3557

    Article  CAS  Google Scholar 

  64. Chatterjee N, Sarkar S, Pal R, Sen AK (2014) Tetr Lett 55(14):2261–2265

    Article  CAS  Google Scholar 

  65. Nefzi A, Ong NA, Houghten RA (2001) Tetr Lett 42(31):5141–5143

    Article  CAS  Google Scholar 

  66. Dadiboyena S, Arfaoui A, Amri H, Piedrafita FJ, Nefzi A (2015) Bioorg Med Chem Lett 25(3):685–689

    Article  CAS  Google Scholar 

  67. Schwarz MK, Tumelty D, Gallop MA (1998) Tetr Lett 39(46):8397–8400

    Article  CAS  Google Scholar 

  68. Lee J, Gauthier D, Rivero RA (1999) J Org Chem 64(9):3060–3065

    Article  CAS  Google Scholar 

  69. Wu CY, Sun CM (2002) Bioorg Med Chem Lett 12(6):959–962

    Article  CAS  Google Scholar 

  70. Herpin TF, Van Kirk KG, Salvino JM, Yu ST, Labaudiniére RF (2000) J Comb Chem 2(5):513–521

    Article  CAS  Google Scholar 

  71. Kidwai M, Venkataramanan R (2004) Chem Heterocycl Compd 40(5):631–634

    Article  CAS  Google Scholar 

  72. Kong KH, Chen Y, Ma X, Chui WK, Lam Y (2004) J Comb Chem 6(6):928–933

    Article  CAS  Google Scholar 

  73. Sharma N, Chundawat TS, Mohapatra SC, Bhagat S (2013) RSC Adv 3(37):16336–16339

    Article  CAS  Google Scholar 

  74. Goff DA, Zuckermann RN (1995) J Org Chem 60(18):5744–5745

    Article  CAS  Google Scholar 

  75. Verdié P, Subra G, Averland-Petit MC, Amblard M, Martinez J (2008) J Comb Chem 10(6):869–874

    Article  CAS  Google Scholar 

  76. Verdié P, Subra G, Feliu L, Sanchez P, Bergé G, Garcin G, Martinez J (2007) J Comb Chem 9(2):254–262

    Article  CAS  Google Scholar 

  77. Mayer JP, Zhang J, Bjergarde K, Lenz DM, Gaudino JJ (1996) Tetr Lett 37(45):8081–8084

    Article  CAS  Google Scholar 

  78. Gerdes JM, Waldmann H (2003) J Comb Chem 5(6):814–820

    Article  CAS  Google Scholar 

  79. Migihashi C, Sato F (2003) J Heterocycl Chem 40(1):143–147

    Article  CAS  Google Scholar 

  80. Hulme C, Ma L, Kumar NV, Krolikowski PH, Allen AC, Labaudiniere R (2000) Tetr Lett 41(10):1509–1514

    Article  CAS  Google Scholar 

  81. Smith RA, Bobko MA, Lee W (1998) Bioorg Med Chem Lett 8(17):2369–2374

    Article  CAS  Google Scholar 

  82. Hulme C, Peng J, Morton G, Salvino JM, Herpin T, Labaudiniere R (1998) Tetr Lett 39(40):7227–7230

    Article  CAS  Google Scholar 

  83. Chen JJ, Golebiowski A, Klopfenstein SR, West L (2002) Tetr Lett 43(22):4083–4085

    Article  CAS  Google Scholar 

  84. Kennedy AL, Fryer AM, Josey JA (2002) Org Lett 4(7):1167–1170

    Article  CAS  Google Scholar 

  85. Jeon MK, Kwon JJ, Kim MS, Gong YD (2008) Synlett 2008(11):1651–1656

    Article  CAS  Google Scholar 

  86. Boojamra CG, Burow KM, Ellman JA (1995) J Org Chem 60(18):5742–5743

    Article  CAS  Google Scholar 

  87. Ettmayer P, Chloupek S, Weigand K (2003) J Comb Chem 5(3):253–259

    Article  CAS  Google Scholar 

  88. Joseph CG, Wilson KR, Wood MS, Sorenson NB, Phan DV, Xiang Z, Witek RM, Haskell-Luevano C (2008) J Med Chem 51(5):1423–1431

    Article  CAS  Google Scholar 

  89. Rivero IA, Peralta M, Heredia S, Madrigal D, Pina-Luis G, Chávez D (2003) Arkivoc 2003(11):27–36

    Article  Google Scholar 

  90. Nefzi A, Ostresh JM, Houghten RA (1997) Tetr Lett 38(28):4943–4946

    Article  CAS  Google Scholar 

  91. Nefzi A, Dooley C, Ostresh JM, Houghten RA (1998) Bioorg Med Chem Lett 8(17):2273–2278

    Article  CAS  Google Scholar 

  92. Moure A, Sanclimens G, Bujons J, Masip I, Alvarez-Larena A, Pérez-Payá E, Alfonso I, Messeguer A (2011) Chem Eur J 17(28):7927–7939

    Article  CAS  Google Scholar 

  93. Krchňák V, Weichsel AS (1997) Tetr Lett 38(42):7299–7302

    Article  Google Scholar 

  94. Giovannoni J, Subra G, Amblard M, Martinez J (2001) Tetr Lett 42(32):5389–5392

    Article  CAS  Google Scholar 

  95. Caroen J, Clemmen A, Kámán J, Backaert F, Goeman JL, Fülöp F, Van der Eycken J (2016) Tetrahedron 72(1):148–160

    Article  CAS  Google Scholar 

  96. Sülli-Vargha H, Schlosser G, Ilaš J (2007) J Peptide Sci 13(11):742–748

    Article  CAS  Google Scholar 

  97. Lampariello LR, Piras D, Rodriquez M, Taddei M (2003) J Org Chem 68(20):7893–7895

    Article  CAS  Google Scholar 

  98. Xu JF, Huang X (2009) J Comb Chem 11(5):938–942

    Article  CAS  Google Scholar 

  99. Cao J, Huang X (2010) J Comb Chem 12(1):1–4

    Article  CAS  Google Scholar 

  100. Huang X, Cao J, Huang J (2009) J Comb Chem 11(4):515–518

    Article  CAS  Google Scholar 

  101. Olsen CA, Christensen C, Nielsen B, Farah MM, Witt M, Clausen RP, Kristensen JL, Franzyk H, Jaroszewski JW (2006) Org Lett 8(15):3371–3374

    Article  CAS  Google Scholar 

  102. Ottesen LK, Olsen CA, Witt M, Jaroszewski JW, Franzyk H (2009) Chem Eur J 15(12):2966–2978

    Article  CAS  Google Scholar 

  103. Li D, Hall DG (2005) Tetrahedron: Asymmetry 16(10):1733–1736

    Article  CAS  Google Scholar 

  104. Eans SO, Ganno ML, Mizrachi E, Houghten RA, Dooley CT, McLaughlin JP, Nefzi A (2015) J Med Chem 58(12):4905–4917

    Article  CAS  Google Scholar 

  105. Vaňková B, Brulíková L, Wu B, Krchňák V (2012) Eur J Org Chem 2012(26):5075–5084

    Article  CAS  Google Scholar 

  106. Ventosa-Andrés P, Barea Ripoll CA, La-Venia A, Krchňák V (2015) Tetr Lett 56(40):5424–5428

    Article  CAS  Google Scholar 

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Acknowledgments

The authors are grateful to project CZ.1.07/2.3.00/20.0009 from the European Social Fund and the National Program of Sustainability (project LO1304).

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Authors and Affiliations

  1. Department of Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of Science, Palacky University, 17. listopadu 12, Olomouc, 771 46, Czech Republic

    Veronika Fülöpová & Miroslav Soural

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  1. Veronika Fülöpová
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  2. Miroslav Soural
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Correspondence to Miroslav Soural .

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  1. University of Notre Dame , Notre Dame, Indiana, USA

    Viktor Krchňák

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Fülöpová, V., Soural, M. (2017). Solid-Phase Synthesis of Seven-Membered Heterocycles with Two Nitrogen Atoms. In: Krchňák , V. (eds) Solid-Phase Synthesis of Nitrogenous Heterocycles. Topics in Heterocyclic Chemistry, vol 52. Springer, Cham. https://doi.org/10.1007/7081_2016_2

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