A convenient and efficient conversion of 2-carboxyheteroarenes into N-(2-thienyl- and 2-selenophenyl)-1-methylpyrrole-2-carboxamides

Arkivoc

Volumn 2000, Issue 1 SPEC.ISS., 2000, Pages 58-62

  Danielli, Filippo ^a   Zanirato, Paolo ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 METHYL N (2 FURANO) 1H PYRROLE 2 CARBOXAMIDE; 1 METHYL N (2 SELENOPHENE) 1H PYRROLE 2 CARBOXAMIDE; 1 METHYL N (2 THIOPHENE) 1H PYRROLE 2 CARBOXAMIDE; 1 METHYL N (5 METHYL 2 THIOPHENE) 1H PYRROLE 2 CARBOXAMIDE; 1 METHYL N (5 TRIMETHYLSILYL 2 SELENOPHENE) 1H PYRROLE 2 CARBOXAMIDE; 1 METHYL N (5 TRIMETHYLSILYL 2 THIOPHENE) 1H PYRROLE 2 CARBOXAMIDE; 1 METHYLPYRROLE; AZIDE; NITROGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRROLE DERIVATIVE; THIOPHENE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; HIGH TEMPERATURE PROCEDURES;

EID: 13544254538     PISSN: 14246376     EISSN: 14246376     Source Type: Journal    
DOI: None     Document Type: Article

References (29)

1. (a) Sheradsky, T. The Chemistry of the Azido Group, Patai, S., Ed.; Interscience: London, 1971, p 331.
2. (b) Scriven, E. F. V.; Turnbull, K. Chem, Rev. 1988, 88, 291.
3. Chemistry and Technology of Isocyanates, Ulrich, H., Ed., Wiley: Chichester, 1996.
4. (a) Spagnolo, P.; Zanirato, P. J. Org. Chem. 1978, 43, 3539.
5. (b) Spinelli, D.; Zanirato, P. J. Chem. Soc. Perkin Trans 2 1993, 1129.
6. Gronowitz, S.; Zanirato, P. J. Chem. Soc. Perkin Trans. 2, 1994, 1815.
7. (a) Davies, D.; Spagnolo, P.; Zanirato, P. J. Chem. Soc. Perkin Trans, 1 1995, 613.
8. (b) Valenti, F.; Zanirato, P. J. Chem. Soc. Perkin Trans 2 1999, 623.
9. For recent reviews on this topic see: (a) Funicello, M.; Spagnolo, P.; Zanirato, P. Acta Chem. Scand. 1993, 47, 231.
10. (b) Becher, J.; Dehaen, W. Acta Chem. Scand. 1993, 47, 244.
11. (a) Smith, P. A. S. Org. React. 1946, 3, 337.
12. (b) Ah-Kow, G.; Paulmier, C.; Pastour, C. Bull. Soc. Chim. Fr. 1976, 151.
13. Binder, D.; Habison, G.; Noe, C.R. Synthesis 1977, 255.
14. Advanced Organic Chemistry, March, J., Ed., Wiley: New York, 4th ed., 1992, 547.
15. (a) Effenberger, F.; Gleiter, R. Chem. Ber. 1964, 97, 472.
16. (b) Alder, R. W.; Chalkley, G. R.; Whiting, M. C., J. Chem. Soc. 1966, 52.
17. Norris, R. K. The Chemistry of Heterocyclic Compounds, Gronowitz, S., Ed, 1990, 44, Part II, 631.
18. Bailey, P. D.; Collier, I. D.; Morgan, K. M., Comprehensive Organic Functional Group Transformation, Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds, Pergamon: Cambridge, 1995, 5, 257.
19. (f)Connell, R. D.; Comprehensive Organic Functional Group Transformation, Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds, Pergamon: Cambridge, 1995, 5, 309.
20. Toselli, M.; Zanirato, P. J. Chem. Soc. Perkin Trans 1 1992, 1101.
21. Gribble, G. W.; Comprehensive Heterocyclic Chemistry II, Katritzky, A. R.; Rees, C. W.; Scriven E. F. V.; Storr, R. C., Eds, Pergamon: Oxford, 1996, 2, 207.
22. (a) Damayanthi, Y.; Reddy, B. S. P.; Lown, J. W. J. Org. Chem. 1999, 64, 290.
23. (b) Christiansen, L. E. E.; Selenophenes ref. 8, p 731.
24. Russel, R. K.; Press, J. B. ref. 8, p 679.
25. Weinstock, J. J. Org. Chem. 1961, 26, 3511.
26. Rault, S.; Cugnon de Sevricourt, M.; Dung, N-H.; Robba, M. J. Heterocyclic Chem. 1981, 18, 739.
27. Azides and Nitrenes; Scriven, E. F. V., Ed., Academic: Orlando, 1984, p 205.
28. Jones, G. B.; Chapman, B. J. ref. 8, 1.
29. Organolithium Methods, Wakefield, B. J., Ed., Academic: London, 1990, p 89.