Regioselective synthesis of thieno[2,3-b]indoles by tandem cyclisation involving sequential sigmatropic rearrangements

Journal of Chemical Research

Volumn , Issue 5, 2006, Pages 289-292

  Majumdar, K C ^a   Alam, Safiul ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

1 methylindoline 2 thione; Fused thiophenes; Indoles; Phase transfer; Sulfoxide rearrangement

Indexed keywords

EID: 33745741410     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823406777411052     Document Type: Article

References (28)

1. Y. Nakashima, Y. Kawashima, F. Amanuma, K. Sota, A. Tanaka and T. Kameyama, Chem. Pharm. Bull., 1984, 32, 4271.
2. M. Taniguchi, T. Anjiki, M. Nakagawa and T. Hino, Chem. Pharm. Bull., 1984, 32, 2544.
3. G. Kobayashi, S. Furukawa, Y. Matsuda and R. Natsuki, Yakugaku Zasshi, 1969, 89, 58.
4. (a) T. Ohmoto and K. Koike, Chem. Pharm. Bull., 1984, 32, 170;
5. (b) M. Shimizu, M. Ishikawa, Y. Komoda, T. Nkajima, K. Yamaguchi and N. Yoneda, Chem. Pharm. Bull., 1984, 32, 463;
6. (c) Y. Endo, K. Shudo, K. Furuhata, H. Ogura, S. Sakai, N. Aimi, Y. Hitotsuyanagi and Y. Koyama, Chem. Pharm. Bull., 1984, 32(1), 358;
7. (d) N. Haider and E. Sotero, Chem. Pharm. Bull., 2002, 50, 1479;
8. (e) S. Sakai, N. Aimi, K. Yamaguchi, Y. Hitotsuyonagi, C. Watanabe, K. Yokose, Y. Koyama, K. Shudo and A. Itai, Chem. Pharm. Bull., 1984, 32, 354.
9. (a) S. Kamijo and Y. Yamamoto, J. Org. Chem., 2003, 68, 4764;
10. (b) R.J. Sundberg, The Chemistry of Indoles, Academic Press, New York, 1970, pp. 438-439;
11. (c) E. Yamanaka, M. One, S. Kasamatsu, N. Aimi and S. Sakai, Chem. Pharm. Bull., 1984, 32, 818.
12. (a) S. Takada and Y. Makisumi, Chem. Pharm. Bull., 1984, 32, 872;
13. (b) S. Takada, N. Ishizuka, T. Sasatani, Y. Makisumi, H. Jyoyama, H. Hatakeyama, F. Asanuma and K. Hirose, Chem. Pharm. Bull., 1984, 32, 877.
14. (a) K.C. Majumdar and B.S. Thyagarajan, J. Chem. Soc., Chem. Commun., 1972, 83;
15. (b) K.C. Majumdar and B.S. Thyagarajan Int. J. Sulfur Chem., 1972, 2A, 93;
16. (c) B. El-Osta, K.C. Majumdar and B.S. Thyagarajan, J. Heterocycl. Chem., 1973, 10, 107;
17. (d) K.C. Majumdar and P. Biswas, Tetrahedron, 1998, 54, 11 603;
18. (e) K.C. Majumdar and B.S. Thyagarajan, Int. J. Sulfur Chem., 1972, 2A, 67.
19. (a) K.C. Majumdar and B.S. Thyagarajan, Int. J. Sulfur Chem., 1972, 2A, 153;
20. (b) J.B. Hillard, K.V. Reddy, K.C. Majumdar and B.S. Thyagarajan, J. Heterocycl. Chem., 1974, 11, 369.
21. (a) K.C. Majumdar and S.K. Ghosh, Tetrahedron Lett., 2002, 43, 2123;
22. (b) K.C. Majumdar and M. Ghosh, Tetrahedron, 2002, 58, 10 047;
23. (c) K.C. Majumdar, U.K. Kundu and S. Ghosh, Tetrahedron., 2002, 58, 10309.
24. (a) B.S. Thyagarajan, J.B. Hillard, K.V. Reddy and K.C. Majumdar, Tetrahedron Lett., 1974, 23, 1999;
25. (b) K.C. Majumdar and S.K. Chattopadhyay, J. Chem. Soc., Chem. Commun., 1987, 524;
26. (c) K.C. Majumdar and S.K. Samanta, Tetrahedron Lett., 2002, 43, 2119;
27. (d) K.C. Majumdar and G.H. Jana, J. Org. Chem., 1997, 62, 1506;
28. (e) K.C. Majumdar, G.H. Jana and U. Das, J. Chem. Soc. Perkin Trans. 1, 1997, 1229.