Benzoannelation of 2-methylindole via 1-N-carboxy-2-methylindole dianion: A direct regiospecific route to substituted and annelated carbazoles

Tetrahedron Letters

Volumn 39, Issue 14, 1998, Pages 2029-2032

  Kumar, U K Syam ^a   Patra, Pranab K ^a   Ila, H ^a   Junjappa, H ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

^b NORTH EASTERN HILL UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; CARBAZOLE DERIVATIVE; INDOLE DERIVATIVE;

AROMATIZATION; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0032473903     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00164-6     Document Type: Article

References (25)

1. 1. Katritzky, A.R.; Akutagawa, K. J. Am. Chem. Soc. 1986, 108, 6808.
2. 2. (a) Reddy, K.R.; Roy, A.; Ila, H.; Junjappa, H. Tetrahedron 1995, 51, 10941;
3. (b) Satyanarayana, J.; Reddy, K.R.; Ila, H.; Junjappa, H. Tetrahedron Lett. 1992, 33, 6173;
4. (c) Pooranchand, D.; Satyanarayana, J.; Ila, H.; Junjappa, H. Synthesis 1993, 241;
5. (d) Balu, M.P.; Pooranchand, D.; Ila, H.; Junjappa, H. Tetrahedron Lett. 1988, 29, 501;
6. (e) Mallik, K.Y.; Mohanta, P.K.; Ila, H.; Junjappa, H. Tetrahedron 1996, 52, 14049;
7. (f) Patra, P.K.; Suresh, J.R.; Ila, H.; Junjappa, H. Tetrahedron Lett. 1997, 38, 3119.
8. 3. Review: (a) Junjappa, H.; Ila, H.; Asokan, C.V. Tetrahedron 1990, 46, 5423;
9. (b) Junjappa, H.; Ila, H. Phosphorus, Sulfur and Silicon 1994, 95-96, 35;
10. See also Suresh, J.R.; Patra, P.K.; Ila, H.; Junjappa, H. Tetrahedron 1997, 53, 14737.
11. 4. (a) Rao, M.V.B.; Satyanarayana, J.; Ila, H.; Junjappa, H. Tetrahedron Lett 1995, 36, 3885;
12. (b) Moody, C.J. Synlett 1994, 681;
13. (c) Kawasaki, T.; Sakamoto, M. J. Indian. Chem. Soc. 1994, 71, 443;
14. (d) Mohanakrishnan, A.K.; Srinivasan, P.C. Tetrahedron Lett. 1993, 34, 1343.
15. 5. Nakatuska, S, -i.; Asano, O.; Goto, T. Heterocycles 1986, 24, 2791.
16. 6. (a) Buttery, C.D.; Jones, R.G.; Knight, D.W. J. Chem. Soc., Perkin Trans. 1 1993, 1425;
17. (b) Sundberg, R.J.; Russel, H.F. J. Org. Chem. 1973, 38, 3324.
18. 7. (a) Castells, J.; Troin, Y.; Diez, A.; Rubiralta, M.; Grierson, D.S.; Husson, H.-P. Tetrahedron 1991, 47, 7911;
19. (b) Nakatuska, O.; Miyazaki, H., Goto, T. Tetrahedron Lett. 1980, 21, 2817.
20. 8. (a) Katritzky, A.R.; Zhang, G.; Xie, L.; Ghiviriga, I. J. Org. Chem. 1996, 61, 7558 and cited references;
21. (b) Bergman, J.; Pelcaman, B. Tetrahedron 1988, 44, 5215;
22. (c) Amat, M.; Coll, D.; Bosch, J. Tetrahedron 1995, 51, 10759.
23. 9. Inagaki, S.; Nishizawa, Y.; Sugiura, T.; Ishihara, H. J. Chem. Soc., Perkin Trans. 1 1990, 179.
24. 31NOS (453.642): C, 79.43; H, 6.88; N, 3.08%. Found: C, 79.21; H, 6.79; N, 2.90%.
25. 11. Katritzky and Akutagawa have shown that 1-N-carboxy-2-ethylindote dianion reacts regiospecifically with methyliodide to give 2-H-propylindole in 95% yield; Ref. 1.