1, 2, 3, 9-tetrahydro-4H-carbazol-4-one and 8, 9-dihydropyrido- [1, 2-a]indol-6(7H)-one from 1H-indole-2-butanoic acid

Journal of Heterocyclic Chemistry

Volumn 46, Issue 2, 2009, Pages 172-177

  Bunce, Richard A ^a   Nammalwar, Baskar ^a  

^a OKLAHOMA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,9 TETRAHYDRO 4H CARBAZOL 4 ONE; 1H INDOLE 2 BUTANOIC ACID; 8,9 DIHYDROPYRIDO [1,2 A]INDOL 6(7H) ONE; BUTYRIC ACID; TOLUENE; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; AROMATIZATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; HEATING; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; SYNTHESIS;

EID: 65349105332     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.22     Document Type: Article

References (41)

1. Bunce, R. A.; Randall, M. H.; Applegate, K. G. Org Prep Proced Int 2002, 34, 493.
2. Augustine, R. L.; Gustavsen, A. J.; Wanat, S. F.; Pattison, I. C.; Houghton, K. S.; Koletar, G. J Org Chem 1973, 38, 3004.
3. Scott, T. L.; Soderberg, B. C. G. Tetrahedron 2003, 59, 6323.
4. Sissouma, D.; Maingot, L.; Collet, S.; Guigant, A. J Org Chem 2006, 22, 8384.
5. Li, X.; Vince, R. Bioorg Med Chem 2006, 14, 2942.
6. (a) Kohno, T.; Yoshikawa, T.; Yoshizawa, A.; Nakamura, I.; Anzai, T.; Satoh, T.; Ogawa, S. Cardiovasc Drug Ther 2005, 19, 347;
7. (b) Romeo, G.; Materia, L.; Pittala, V.; Modica, M.; Salerno, L.; Siracusa, M.; Russo, F.; Minneman, K. P. Bioorg Med Chem 2006, 14, 5211.
8. (a) Elz, S.; Heil, W. L. Bioorg Med Chem Lett 1995, 5, 667;
9. (b) Scott, T. L.; Soderberg, B. C. G. Tetrahedron Lett 2002, 43, 1621.
10. Kato, M.; Ito, K.; Takasugi, H. Eur. Pat., EP451538, 1991; Chem Abstr 1992, 116, 207822.
11. (a) Kato, M.; Ito, K.; Nishino, S.; Yamakuni, H.; Takasugi, H. Chem Pharm Bull 1994, 42, 2546;
12. (b) Kato, M.; Nishino, S.; Ito, K.; Takasugi, H. Chem Pharm Bull 1995, 43, 1346.
13. (a) Czeskis, B. A.; Wheeler, W. J. J Label Compd Radiopharm 2005, 48, 407;
14. (b) Clemo, G.R.; Felton, D. G. I. J Chem Soc 1951, 700.
15. Oikawa, Y.; Yonemitsu, O. J Org Chem 1977, 42, 1213.
16. (a) Wender, P. A.; White, A. W. Tetrahedron 1983, 39, 3767;
17. (b) Kudzma, L. V. Synthesis 2003, 1661.
18. (a) Osuka, A.; Mori, Y.; Suzuki, H. Chem Lett 1982, 2031;
19. (b) Yan, S.; Wu, H.; Wu, N.; Jiang, Y. Synlett 2007, 2699.
20. Iida, H.; Yuasa, Y.; Kibayashi, C. J Org Chem 1979, 44, 1236.
21. (a) Scott, T. L.; Burke, N.; Carrero-Martrnez, G.; Soderberg, B. C. G. Tetrahedron 2007, 63, 1183;
22. (b) S0rensen, U. S.; Pombo-Villar, E. Helv Chim Acta 2004, 87, 82;
23. Wang, H.-M.; Chou, H.-L.; Chen, L.-C. J Chin Chem Soc (Taipei) 1995, 42, 593;
24. Mori, M.; Uozumi, Y.; Shibasaki, M. Heterocycles 1992, 33, 819;
25. (e) Sakamoto, S.; Nagano, T.; Kondo, Y.; Yamanaka, H. Synthesis 1990, 215.
26. Davidson, D.; Bernhard, S. A. J Am Chem Soc 1948, 70, 3426.
27. Mehta, A.; Jaouhari, R.; Benson, T. J.; Douglas, K. T. Tetrahedron Lett 1992, 33, 5441.
28. (a) Oikawa, Y.; Sugano, K.; Yonemitsu, O. J Org Chem 1978, 43, 2087;
29. (b) Oikawa, Y.; Yoshioka, T.; Sugano, K.; Yonemitsu, O. Organic Syntheses; Wiley-Interscience: New York, NY; Coll. Vol. 7, pp 359-361.
30. (a) Sheehan, J. C.; Cruickshank, P. A.; Boshart, G. L. J Org Chem 1961, 26, 2525;
31. (b) Kopple, K. D.; Nitecki, D. E. J Am Chem Soc 1962, 84, 4457.
32. The use of a larger excess of 4-(dimethylamino)pyridine promotes side reactions that generate more complex product mixtures.
33. (a) Several other reagent combinations did not afford satisfactory results for the lactamization. All conditions listed below were run in dichloromethane and each was tried with added triethylamine and/or 4-(dimethylamino)pyridine;
34. (b) N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide alone: see ref. 19b;
35. N-(3-Dimethylaminopropyl)- N′-ethylcarbodiimide with 1-hydroxybenzotriazole: Harigawa, D.; Neya, M.; Miyazaki, Y.; Hemmi, K.; Hashimoto, M. J Chem Soc Chem Commun 1984, 1676;
36. Polymer-bound N-benzyl-N′-cyclohexylcarbodiimide: LeBas, M.-D. H.; McKinley, N. F.; Hogan, A.-M. L.; O'Shea, D. F. J Comb Chem 2005, 7, 503;
37. (e) N, N′-Dicyclohexylcarbodiimide appeared to promote lactam formation, but N, N′-dicyclohexylurea and excess carbodiimide could not be removed from the product.
38. Still, W. C.; Kahn, M.; Mitra, A. J Org Chem 1978, 43, 2923.
39. Mohri, K.; Oikawa, Y.; Hirao, K.; Yonemitsu, O. Hetero-cycles 1982, 19, 515.
40. Julia, M.; Bagot, J. Bull Soc Chim Fr 1964, 1924.
41. Crenshaw, M. D.; Zimmer, H. J Heterocyclic Chem 1984, 21, 623.