Preliminary studies on the Michael addition of quinones to nitroolefins: (6bR,10aS)-7,8,9,10,10a,11-hexahydro-6bH-benzo[a]carbazole-5,6-diones, (4aR,11bS)-1,2,3,4,4a,5-hexahydro-11bH-benzo[b]carbazole-6,11-diones, and 1,2,3,4-tetrahydro-5H-benzo[b]carbazole-6,11-diones

Synlett

Volumn , Issue 9, 2007, Pages 1399-1402

  Barcia, José C ^a   Otero, José M ^a   Estévez, Juan C ^a   Estévez, Ramon J ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Annulations; Asymmetric synthesis; Cyclization; Indoles; Michael additions; Quinones

Indexed keywords

(4A,11B) 1,2,3,4,4A,5 HEXAHYDRO 11BH BENZO[B]CARBAZOLE 6,11 DIONE DERIVATIVE; (6B,10A) 7,8,9,10,10A,11 HEXAHYDRO 6BH BENZ[A]CARBAZOLE 5,6 DIONE DERIVATIVE; 1,2,3,4 TETRAHYDRO 5H BENZO[B]CARBAZOLE 6,11 DIONE DERIVATIVE; NAPHTHOQUINONE; NITRO DERIVATIVE; NITROOLEFIN DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MICHAEL ADDITION;

EID: 34250788154     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-980356     Document Type: Article

References (29)

1. (a) Barret, A. G. M.; Graboski, G. G. Chem. Rev. 1986, 86, 751.
2. (b) Nitroalkanes and Nitroalkenes in Synthesis, In Tetrahedron Symposia-in-Print; Barret, A. G. M., Ed.Tetrahedron 1990, 46, 7313.
3. (c) Noboru, O. In The Nitro Group in Organic Synthesis; Feuer, H., Ed.; Organic Nitro Chemistry Series, Wiley-VCH: New York, 2001.
4. (a) The Chemistry of Functional Groups: The Chemistry of The Quinoid Compounds; Patai, S.; Rappoport, Z., Eds.; Wiley: New York, 1988.
5. (b) Thomson, R. H. Naturally Occurring Quinones, 4th ed.; Chapman and Hall: London, 1997.
6. Cheng, C. C. Structural Aspects of Antineoplastic Agents - A New Approach, In Progress in Medicinal Chemistry, Vol. 25; Ellis, G. P.; West, G. B., Eds.; Elsevier: Amsterdam, 1988, pp 35-83.
7. (a) Gould, S. J. Chem. Rev. 1997, 97, 2499.
8. (b) Marco-Contelles, J.; Molina, M. Curr. Org. Chem. 2003, 7, 1433.
9. Harwood, J. S.; Harwood, C. A. J. Org. Chem. 2004, 69, 5128.
10. Yu, M.; Malinakova, H. C.; Stagliano, K. N. J. Org. Chem. 2006, 71, 6648.
11. (a) Estévez, J. C.; Estévez, R. J.; Castedo, L. Tetrahedron Lett. 1993, 34, 6479.
12. (b) Cruces, J.; Estévez, J. C.; Castedo, L.; Estévez, R. J. Tetrahedron Lett. 2001, 42, 4825.
13. (c) Cruces, J.; Martínez, E.; Treus, M.; Martínez, L. A.; Estévez, J. C.; Estévez, R. J.; Castedo, L. Tetrahedron 2002, 58, 3015.
14. (d) Barcia, J. C.; Cruces, J.; Estévez, J. C.; Estévez, R. J.; Castedo, L. Tetrahedron Lett. 2002, 43, 5141.
15. (e) Fernández, M.; Barcia, C.; Estévez, J. C.; Estévez, R. J.; Castedo, L. Synlett 2004, 267.
16. (f) Otero, J. M.; Barcia, J. C.; Estévez, J. C.; Estévez, R. J. Tetrahedron: Asymmetry 2005, 16, 11.
17. Corey, E. J.; Estreicher, H. J. Am. Chem. Soc. 1978, 100, 6294.
18. +].
19. Kobayasi, K.; Taki, T.; Kawakita, M.; Uchida, M.; Morikawa, O.; Konishi, H. Heterocycles 1999, 51, 349.
20. For previous similar cyclizations leading to oxygen heterocycles, see: (a) Lee, Y. R.; Kang, K. Y.; Lee, G. J.; Lee, W. K. Synthesis 2003, 1977.
21. (b) Lee, Y. R.; Kim, B. S. Synth. Commun. 2003, 33, 4123.
22. (c) Nair, W.; Treesa, P. M.; Maliakal, D.; Rath, N. P. Tetrahedron 2001, 57, 7705.
23. (a) Kobayashi, K.; Takeuchi, H.; Seko, S.; Suginome, H. Helv. Chim. Acta 1991, 74, 1091.
24. (b) Sullivan, P. J.; Moreno, R.; Murphy, W. S. Tetrahedron Lett. 1992, 33, 535.
25. (c) Kobayashi, K.; Takeuchi, H.; Seko, S.; Kanno, Y.; Kujime, S. H.; Suginome, S. Helv. Chim. Acta 1993, 76, 2942.
26. (d) Mithani, S.; Weeratunga, G.; Taylor, N. J.; Dmitrienko, G. I. J. Am. Chem. Soc. 1994, 116, 2209.
27. (e) Tanaka, K.; Takanohashi, A.; Morikawa, O.; Konishi, H.; Kobayashi, K. Heterocycles 2001, 55, 1561.
28. (f) Wu, Y.-L.; Chuang, C.-P.; Lin, P.-Y. Tetrahedron 2001, 57, 5543.
29. Kitani, Y.; Morita, A.; Kumamoto, T.; Ishikawa, T. Helv. Chim. Acta 2002, 85, 1186.