Lewis acid-promoted annulation of o-quinonediimines by allylstannane: A facile synthesis of quinoxaline derivatives

Organic Letters

Volumn 6, Issue 25, 2004, Pages 4743-4745

  Nair, Vijay ^a   Dhanya, R ^a   Rajesh, C ^a   Bhadbhade, Mohan M ^b   Manoj, K ^b  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2 QUINONEDIIMINE; ALKANE DERIVATIVE; IMINE; LEWIS ACID; NITROGEN; QUINOXALINE DERIVATIVE; STANNANE; UNCLASSIFIED DRUG;

ADDITION REACTION; ALLYLATION; ANNULATION REACTION; ARTICLE; SYNTHESIS;

EID: 11444256674     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048004m     Document Type: Article

References (24)

1. For a review on the chemistry of quinones, see: The Chemistry of Quinonoid Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: New York, 1988; Vol. 2, Parts 1 and 2.
2. (a) Nair, V.; Kumar, S. Synlett 1996, 1035.
3. (b) Nair, V.; Kumar, S. J. Chem. Soc., Chem. Commun. 1994, 1341.
4. (c) Nair, V.; Kumar, S. J. Chem. Soc., Perkin Trans. 1 1996, 443.
5. Friedrichsen, W.; Bottcher, A. Heterocycles 1981, 16, 1009 and references therein.
6. Friedrichsen, W.; Schmidt, R. Liebigs Ann. Chem. 1978, 1129.
7. (a) Friedrichsen, W.; Oeser, H. G. Liebigs Ann. Chem. 1978, 1139.
8. (b) Friedrichsen, W.; Oeser, H. G. Liebigs Ann. Chem. 1978, 1146.
9. (c) Friedrichsen, W.; Oeser, H. G. Liebigs Ann. Chem. 1978, 1161.
10. (a) Nair, V.; Rajesh, C.; Dhanya, R.; Vinod, A. U. Tetrahedron Lett. 2001, 42, 2045.
11. (b) Nair, V.; Rajesh, C.; Dhanya, R.; Rath, N. P. Tetrahedron Lett. 2002, 43, 5349.
12. (c) Nair, V.; Rajesh, C.; Dhanya, R.; Rath, N. P. Org. Lett. 2002, 4, 953. 39, 5627.
13. (c) Nair, V.; Rajesh, C.; Dhanya, R.; Rath, N. P. Org. Lett. 2002, 4, 953. 39, 5627.
14. (a) Herndon, J. W. J. Am. Chem. Soc. 1987, 109, 3165.
15. (b) Herndon, J. W.; Wu, C.; Harp, J. J.; Kreutzer, K. A. Synlet 1991, 1.
16. (c) Herndon, J. W.; Wu, C. Tetrahedron Lett. 1989, 30, 5745.
17. Patel, M.; Mc Hugh, R. J., Jr.; Cordova, B. C.; Klabe, R. M.; Erickson-Vitanen, S.; Trainor, G. L.; Rodgers, J. D. Bioorg. Med. Chem Lett. 2000, 10, 1729.
18. Guillon, J.; Dallemagne, P.; Pfeiffer, B.; Renard, P.; Manechez, D. Kervran, A.; Rault, S. Eur. J. Med. Chem. 1998, 33, 293.
19. Kim, K. S.; Qian, L.; Bird, J. E.; Dickinson, K. E. J.; Moreland, S.; Schaeffer, T. R.; Waldron, T. L.; Delaney, C. L.; Weller, H. N.; Miller, A. V. J. Med. Chem. 1993, 36, 2335.
20. Adams, R.; Winnick, C. N. J. Am. Chem. Soc. 1951, 73, 5687.
21. 4. It was concentrated, and the residue on silica gel chromatography with 15% ethyl acetate in hexane afforded the tetrahydroquinoxaline derivative 3a in 147 mg (98%).
22. Adams, R.; Way, J. W. J. Am. Chem. Soc. 1954, 76, 2763.
23. Boue, S.; Gielen, M.; Nasielski, J. J. Organomet. Chem. 1967, 9, 443.
24. Herndon, J. W.; Wu, C. Tetrahedron Lett. 1989, 30, 6461.