Regioselective synthesis of thieno[3,2-β] indole by tandem cyclization of 1-acetyl-3-(4′-aryloxybut-2′-ynylthio) indole (experimental section)

Letters in Organic Chemistry

Volumn 3, Issue 3, 2006, Pages 250-252

  Majumdar, Krishna C ^a   Alam, Safiul ^a   Muhuri, Sanjukta ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

2,3 sigmatropic rearrangement; 3,3 sigmatropic rearrangement; m CPBA; Regioselective synthesis; Sulfoxide rearrangement; Thieno 3,2 b indole

Indexed keywords

EID: 33746151176     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017806775789868     Document Type: Article

References (24)

1. a) Joule, J. A. Science of Synthesis (Houben-Weyl, Methods of Molecular Transformations); Georg Thieme Verlag: Stuttgart, 2000; Vol. 10, pp. 361;
2. b) Bonjoch, J.; Bosch, J. Alkaloids. 1996, 48, 75;
3. c) Sundberg, R. J. Indoles; Academic Press: London, 1996;
4. d) Saxton, J. E. The Chemistry of Heterocyclic Compounds, Academic Press: New York, 1994, 25, Part IV;
5. e) Chadwick, D. J.; Jones, R.A.; Sundberg, R. J. Conprehensive Heterocyclic Chemistry, Pergamon: Oxford, 1984, Vol. 4, pp 155.
6. a) Szantay, C. Pure Appl. Chem. 1990, 62, 1299;
7. b) Hibino, S.; Choshi, T. Nat. Pod. Rep. 2002, 19, 148 and earlier reviews in the series.
8. Recent review: Gribble, G. W. J. Chem. Soc., Perkin Trans. 1, 2000, 1045.
9. a) Majumdar, K. C.; Thyagaranjan, B. S. Int J Sulfur Chem. 1972, 2A, 67;
10. b) Majumdar, K. C.; Thyagaranjan, B, S. Int J. Sulfur Chem. 1972, 2A, 93;
11. c) El-Osta, B.; Majumdar, K.C.; Thyagaranjan, B. S. Int J Heterocyclic Chem. 1973, 10, 107.
12. a) Hillard, J.B.; Thyagranjan. B. S.; Reddy, K V.; Majumdar, K. C. Tetrahedron Lett. 1974, 1999;
13. b) Hillard, J. B.; Reddy, K V.; Majumdar, K. C.; Thyagaranjan, B. S. J Heterocyclic Chem. 1974,11, 369;
14. c) Thyagaranjan, B. S.; Majumdar, K. C. J Heterocyclic Chem. 1975, 12, 43.
15. a) Majumdar, K. C.; Chattopadhyay, S. K. J. Chem. Soc. Chem. Commun. 1987. 524;
16. b) Majumdar, K. C.; Chattopadhyay, S. K; Khan, A. T. J. Chem. Soc. Perkin Trans. 1, 1989, 1285;
17. c) Majumdar, K. C.; Ghosh, S. K. J. Chem. Soc. Perkin Trans. 1, 1994, 2889;
18. d) Majumdar, K. C.; Ghosh, S. K. Tetrahedron Lett. 2002, 43, 2123;
19. e) Majumdar, K. C.; Chattopadhyay, S. K; Ghosh, M. Lett. Org. Chem. 2005, 2, 231.
20. a) Majumdar, K. C.; Das, U.; Jana, N. K. J. Org. Chem. 1998, 63, 3550;
21. b) Majumdar, K. C.; Biswas, P. Tetrahedron. 1998, 54, 11603;
22. c) Majumdar, K. C.; Biswas, P. Tetrahedron. 1999, 55, 1449;
23. d) Majumdar, K. C.; Samanta, S. K. Tetrahedron Lett. 2002, 43, 2119.
24. Harris, R. L. N. Tetrahedron Lett. 1969, 4465.