Microwave-assisted synthesis of pyrrole-2-carboxamides

Synlett

Volumn , Issue 9, 2005, Pages 1405-1408

  Werner, Stefan ^a   Iyer, Pravin S ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

Heterocycles; Library synthesis; Microwave irradiation; Paal Knorr reaction; Pyrroles

Indexed keywords

AMIDE; PYRROLE DERIVATIVE;

ARTICLE; COMPARATIVE STUDY; CYCLIZATION; HEATING; MICROWAVE IRRADIATION; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS; TECHNIQUE;

EID: 20544464835     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-868512     Document Type: Article

References (31)

1. (a) Ruault, P.; Pilard, J. F.; Touaux, B.; Texier-Boullet, F.; Hamelin, J. Synlett 1994, 935.
2. (b) Danks, T. N. Tetrahedron Lett. 1999, 40, 3957.
3. (c) Minetto, G.; Raveglia, L. F.; Taddei, M. Org. Lett. 2004, 6, 389.
4. (d) Bharadwaj, A. R.; Scheidt, K. A. Org. Lett. 2004, 6, 2465.
5. (a) Forenza, S.; Minale, L.; Riccio, R. J. Chem. Soc., Chem. Commun. 1971, 1129.
6. (b) Garcia, E. E.; Benjamin, L. E.; Fryer, R. I. J. Chem. Soc., Chem. Commun. 1973, 78.
7. (c) Lindel, T.; Hochgürtel, M. J. Org. Chem. 2000, 65, 2806.
8. (a) Albizati, K. F.; Faulkner, D. J. J. Org. Chem. 1985, 50, 4163.
9. (b) Xu, Y.; Yakushijin, K.; Horne, D. A. Tetrahedron Lett. 1996, 37, 8121.
10. (a) Cafieri, F.; Fattorusso, E.; Mangoni, A.; Taglialatela-Scafati, O. Tetrahedron Lett. 1995, 36, 7893.
11. (b) Marchais, S.; Mourabit, A.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron Lett. 1999, 40, 5519.
12. (a) Palermo, J. A.; Brasco, M. F. R.; Seldes, A. M. Tetrahedron 1996, 52, 2727.
13. (b) Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165.
14. (a) Bailly, C.; Chaires, J. B. Bioconjugate Chem. 1998, 9, 513.
15. (b) Dyatkina, N. B.; Roberts, C. D.; Keicher, J. D.; Dai, Y.; Nadherny, J. P.; Zhang, W.; Schmitz, U.; Kongpachith, A.; Fung, K.; Novikov, A. A.; Lou, L.; Velligan, M.; Khorlin, A. A.; Chen, M. S. J. Med. Chem. 2002, 45, 805.
16. (c) Bürli, R. W.; Ge, Y.; White, S.; Baird, E. E.; Touami, S. M.; Taylor, M.; Kaizerman, J. A.; Moser, H. E. Bioorg. Med. Chem. Lett. 2002, 12, 2591.
17. (a) Lombardi, P.; Crisanti, A. Pharmacol. Ther. 1997, 76, 125.
18. (b) Pinna, G. A.; Pirisi, M. A.; Chelucci, G.; Mussinu, J. M.; Murineddu, G.; Loriga, G.; D'Aquila, P. S.; Serra, G. Bioorg. Med. Chem. 2002, 10, 2485.
19. (c) Silvestri, R.; La Regina, G.; De Martino, G.; Artico, M.; Befani, O.; Palumbo, M.; Agostinelli, E.; Turini, P. J. Med. Chem. 2003, 46, 917.
20. (d) Manley, J. M.; Kaiman, M. J.; Conway, B. G.; Ball, C. C.; Havens, J. L.; Vaidyanathan, R. J. Org. Chem. 2003, 68, 6447.
21. (a) Bergtrom, D. E.; Zhang, P.; Johnson, W. T. Nucleosides, Nucleotides Nucleic Acids 1996, 15, 59.
22. (b) Nairne, R. J. D.; Pickering, L.; Smith, C. L. Tetrahedron Lett. 2002, 43, 2289.
23. (a) Knorr, L. Chem. Ber. 1884, 17, 1635.
24. (b) Paal, C. Chem. Ber. 1885, 18, 367.
25. (a) Brummond, K. M.; Mitasev, B. Org. Lett. 2004, 6, 2245.
26. (b) Brummond, K. M.; Curran, D. P.; Mitasev, B.; Fischer, S. J. Org. Chem. 2005, in press.
27. (a) Suzuki, M.; Kimura, Y.; Terashima, S. Bull. Chem. Soc. Jpn. 1986, 59, 3559.
28. (b) Stetter, H.; Skobel, H. Chem. Ber. 1987, 120, 643.
29. After 10-15 seconds, the desired temperature was reached and only less than 15 W were applied for the rest of the time.
30. 4. After evaporation of the solvents, the crude material was purified by column chromatography. (d) Reaction under inert gas conditions: The microwave tube was flushed with argon prior to irradiation in the microwave.
31. 5FNa: 595.2537; found: 596.2544.