Application of 7-endo-trig Pictet-Spengler cyclization to the formation of the benzazepine ring: Synthesis of benzazepinoindoles

European Journal of Organic Chemistry

Volumn , Issue 9, 2009, Pages 1309-1312

  Sharma, Sudhir K ^a   Sharma, Sunil ^a   Agarwai, Piyusli K ^a   Kundu, Bijoy ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Cyclization; Fused ring systems; Nitrogen heterocycles; Polycycles

Indexed keywords

EID: 63449115780     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200801201     Document Type: Article

References (19)

1. G. Cimino, S. De Rosa, D. De Stefano, L. Mazzarella, R. Puliti, G. Sodano, Tetrahedron Lett. 1982, 23, 767 - 768.
2. C. Schultz, A. Link, M. Leost, D. W. Zaharevitz, R. Gussio, E. A. Sausville, L. Meijer, C. Kunick, J. Med. Chem. 1999, 42, 2909 - 2919.
3. I. K. Buolamwini, Curr. Pharm. Des. 2000, 6, 379 - 392.
4. Y. Wan, W. Hur, C. Y. Cho, Y. Liu, F. J. Adrian, O. Lozach, S. Bach, T. Mayer, D. Fabbro, L. Meijer, N. S. Gray, Chem. Biol. 2004, 11, 247 - 259.
5. a) Y. Wan, W. Hur, C. Y. Cho, Y. Liu, F. I Adrian, O. Lozach, S. Bach, T. Mayer, D. Fabbro, L. Meijer, N. S. Gray, Chem. Biol. 2004, 11, 247 - 259;
6. b) J. J. Breton, M.C. Chabot-Fletcher, J. Pharmacol. Exp. Then 1997, 282, 459 - 466;
7. c) L. Meijer, A.- M. W. H. Thunnissen, A. W. White, M. Gamier, M. Nikolic, L.-H. Tsai, J. Walter, K. E. Cleverley, P. C. Salinas, Y. Z. Wu, X Biernat, E. M. Mandelkow, S.-H. Kim, G. R. Pettit, Chem. Biol. 2000, 7, 51- 63;
8. d) D. Tasdemir, R. Mallon, M. Greenstein, L. R. Feldberg, S. C. Kim, K. Collins, D. Wojcie- chowicz, G. C. Mangalindan, G. P. Conceptión, M. K. Harper, C. M. Ireland, J. Med. Chem. 2002, 45, 529 - 532;
9. e) V. Sharma, T. A. Lansdell, G. Jin, J. J. Tepe, J. Med. Chem. 2004, 47, 3700 - 3703.
10. a) B. Kundu, D. Sawant, R. Chhabra, J. Comb. Chem. 2005, 7, 317 - 321;
11. b) S. Duggineni, D. Sawant, B. Saha, B. Kundu, Tetrahedron 2006, 62, 3228 - 3241;
12. c) S. Sharma, B. Saha, D. Sawant, B. Kundu, J. Comb. Chem. 2007, 9, 783 - 792.
13. a) B. Kundu, D. Sawant, P. Partani, A. P. Kesarwani, J. Org. Chem. 2005, 70, 4889 - 4892;
14. b) S. Gracia, J. Schulz, S. Pellet-Rostaing, M. Lemaire, Synlell 2008, 1852 - 1856;
15. c) J. Kraxner, H. Hubner, P. Gmeiner, Arch. Pharm. Weinheim, Ger.) 2000, 333, 287 - 292.
16. U. Nubbemeyer, Top. Curr. Chem. 2001, 216, 125 - 196.
17. M. Westermaier, H. Mayr, Org. Lett. 2006, 8, 4791- 4794.
18. T.-L. Ho, D.-G. Jou, Helv. Chim. Acta 2002, 85, 3823 - 3827.
19. E. D. Cox, X Cook, Chem. Rev. 1995, 95, 1797 - 1842.