N-vinyl- and C-vinylpyrroles from azafulvenium methides. Flash vacuum pyrolysis route to 5-oxo-5H-pyrrolizines and 1-azabenzo[f]azulenes

Journal of Organic Chemistry

Volumn 70, Issue 17, 2005, Pages 6629-6638

  Pinho E Melo, Teresa M V D ^a   Soares, Maria I L ^a   Rocha Gonsalves, Antonio M D'A ^a   Paixão, José A ^b   Beja, Ana Matos ^b   Silva, Manuela Ramos ^b  

^a UNIVERSITY OF COIMBRA   (Portugal)

^b UNIVERSITY OF COIMBRA   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR STRUCTURE; PYROLYSIS; REACTION KINETICS; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

AZAFULVENIUM METHIDES; FLASH VACUUM PYROLYSIS; THERMAL EXTRUSION; X-RAY STRUCTURES;

NITROGEN COMPOUNDS;

1 AZABENZO[F]AZULENE DERIVATIVE; 5 OXO 5H PYRROLIZINE DERIVATIVE; AZAFULVENIUM METHIDE DERIVATIVE; AZULENE DERIVATIVE; PYRROLE DERIVATIVE; PYRROLO[1,2 C]THIAZOLE 2,2 DIOXIDE DERIVATIVE; SULFUR DIOXIDE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; VINYLPYRROLE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CYCLIZATION; DIPOLE; ELECTROCYCLIZATION; FLASH VACUUM PYROLYSIS; PYROLYSIS; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; THERMAL ANALYSIS; X RAY ANALYSIS;

EID: 23644462274     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050480i     Document Type: Article

References (16)

1. (a) Sutcliffe, O. B.; Storr, R. C.; Gilchrist, T. L.; Rafferty, P.; Crew, A. P.A. Chem. Commun. 2000, 675-676.
2. (b) Sutcliffe, O. B.; Storr, R. C.; Gilchrist, T. L.; Rafferty, P. J. Chem. Soc., Perkin Trans. 1 2001, 1795-1806.
3. (a) Pinho e Melo, T. M. V. D.; Barbosa, D. M.; Ramos, P. J. R. S.; Rocha Gonsalves, A. M. d'A.; Gilchrist, T. L.; Beja, A. M.; Paixão, J. A.; Silva, M. R.; Alte da Veiga, L. J. Chem. Soc., Perkin Trans, 1 1999, 1219-1223.
4. (b) Pinho e Melo, T. M. V. D.; Soares, M. I. L.; Barbosa, D. M.; Rocha Gonsalves, A. M. d'A.; Paixão, J. A.; Beja, A. M.; Silva, M. R.; Alte da Veiga, L. Tetrahedron 2000, 56, 3419-3424.
5. (c) Pinho e Melo, T. M. V. D.; Soares, M. I. L.; Rocha Gonsalves, A. M. d'A.; Paixão, J. A.; Beja, A. M.; Silva, M. R.; Alte da Veiga, L.; Costa Pessoa, J. J. Org. Chem. 2002, 67, 4045-4054.
6. (d) Pinho e Melo, T. M. V. D.; Gomes, C. S. B.; Rocha Gonsalves, A. M. d'A.; Paixão, J. A.; Beja, A. M.; Ramos Silva, M.; Alte da Veiga, L. Tetrahedron 2002, 58, 5093-5102.
7. Pinho e Melo, T. M. V. D.; Soares, M. I. L.; Rocha Gonsalves, A. M. d'A.; McNab, H. Tetrahedron Lett. 2004, 45, 3889-3893.
8. Experimental procedure described for the formylation of 2-(pyridin-3-yl)-1,3-thiazolidine in: Fabre, J.-L.; Farge, D.; James, C.; Lavé, D. US Patent 4,529,728.
9. Experimental procedure described for the synthesis of 7-cyano-3-(3-pyridyl)-1H,3,H-pyrrolo[1,2-c]thazole in: Rajoharison, H. G., US Patent 5,124,459.
10. (a) McNab, H. J. Chem. Soc., Perkin Trans, 1 1987, 657-659.
11. (b) McNab, H.; Parson, S.; Stevenson, E. J. Chem. Soc., Perkin Trans. 1 1999, 2047-2048.
12. (c) McNab, H. Aldrichim. Acta 2004, 37, 19-26.
13. (d) Trofimov, B. A.; Sobenina, L. N.; Demenev, A. P.; Mikhaleva, A. I. Chem. Rev. 2004, 104, 2481-2506.
14. Gross, G.; Wentrup, C. J. Chem. Soc., Perkin Trans. 1 1982, 360-361.
15. Padwa, A.; Fryxell, G. E.; Gasdaska, J. R.; Venkatramanan, M. K.; Wong, G. S. K. J. Org. Chem. 1989, 54, 644-652.
16. Compound previously described in ref 1 as a yellowish oil.