Synthesis and reactions of a stable o-quinoid 10-π-electron system, furo[3,4-c]pyridine

Journal of Organic Chemistry

Volumn 65, Issue 10, 2000, Pages 3111-3115

  Sarkar, Tarun K ^a   Ghosh, Sunil K ^a   Chow, Tahsin J ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

^b INSTITUTE OF CHEMISTRY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR STABILITY; SYNTHESIS;

EID: 0034685856     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991886w     Document Type: Article

References (20)

1. Rodrigo, R. Tetrahedron 1988, 44, 2093.
2. Padwa, A. Chem. Commun. 1998, 1417.
3. Wiersum, U. E.; Eldred, C. D. Tetrahedron Lett. 1977, 18, 1741.
4. Muller, P.; Schaller, J.-P. Tetrahedron Lett. 1989, 30, 1507.
5. Chen, C.-W.; Beak, P. J. Org. Chem. 1986, 51, 3325.
6. Hamaguchi, M.; Ibata, T. Chem. Lett. 1976, 287.
7. For giving this reaction a name reaction status, see: Peters, O.; Friedrichsen, W. Tetrahedron Lett. 1995, 36, 8581.
8. Sarkar, T. K.; Ghosh, S. K.; Nandy, S. K.; Chow, T. J. Tetrahedron Lett. 1999, 40, 397.
9. Carly, P. R.; Compernolle, F.; Hoornaert, G. J. Tetrahedron Lett. 1995, 36, 2113.
10. Padwa, A.; Dimitroff, M.; Wasterson, A. G.; Wu, T. J. Org. Chem. 1997, 62, 4088. See also Padwa, A.; Dimitroff, M.; Wasterson, A. G.; Wu, T. J. Org. Chem. 1998, 63, 3986.
11. Padwa, A.; Dimitroff, M.; Wasterson, A. G.; Wu, T. J. Org. Chem. 1997, 62, 4088. See also Padwa, A.; Dimitroff, M.; Wasterson, A. G.; Wu, T. J. Org. Chem. 1998, 63, 3986.
12. Bobbitt, J. M.; Scola, D. A. J. Org. Chem. 1960, 25, 560.
13. Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7382.
14. Baum, J. S.; Shook, D. A.; Davies, H. M. L.; Smith, H. D. Synth. Commun. 1987, 17, 1709.
15. All calculations were done using the semiempirical method PM3 implanted on Spartan with full geometry optimization. Stewart, J. J. P. J. Comput.-Aided Mol. Des. 1990, 4, 1.
16. Sarkar, T. K.; Ghosh, S. K.; Nigam, G. D.; Chinnakali, K.; Fun, H.-K. Acta Crystallogr. 1999, C55, 1140.
17. Sarkar, T. K.; Ghosh, S. K.; Nigam, G. D.; Chinnakali, K.; Fun, H.-K. Acta Crystallogr. 1999, C55, 1138.
18. Newman, M. S.; Hung, W. M. J. Org. Chem. 1975, 40, 262.
19. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley-Interscience: New York, 1976.
20. Vernier, J.-M.; Holsenback, H.; Cosford, N. D. P.; Whitten, J. P.; Menzaghi, F.; Reid, R.; Rao, T. S.; Sacaan, A. I.; Lloyd, G. K.; Suto, C. M.; Chavez-Noriega, L. E.; Washburn, M. S.; Urrutia, A.; Mcdonald, I. A. Bioorg. Med. Chem. Lett. 1998, 8, 2173.