Synthesis of 4-cyano pyrroles via mild Knorr reactions with β-ketonitriles

Organic Process Research and Development

Volumn 10, Issue 5, 2006, Pages 899-904

  Magnus, Nicholas A ^a   Staszak, Michael A ^a   Udodong, Uko E ^a   Wepsiec, James P ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33750129787     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op060104f     Document Type: Article

References (19)

1. Albaugh, P. A.; Dominguez-Manzanares, E.; Hong, J. E.; Hornback, W. J.; Jiang, D.; Ornstein, P. L.; Thompson, M. L.; Tromiczak, E. C.; Wu, Z.; Zarrinmayeh, H.; Zimmerman, D. M.; Castano-Mansanet, A. M.; Huffman, L. G.; Miller, B. D. Pyrrole and Pyrazole derivatives as Potentiators of Glutamate Receptors. (Eli Lilly & Co., Indiana, USA) PCT Int. Appl. WO 2005/040110, 2005 and references cited therein.
2. Magnus, N. A.; Aikins, J. A.; Cronin, J. S.; Diseroad, W. D.; Hargis, A. D.; LeTourneau, M. E.; Parker, B. E.; Reutzel-Edens, S. M.; Schafer, J. P.; Staszak, M. A.; Stephenson, G. A.; Tameze, S. L.; Zollars, L. M. H. Org. Process Res. Dev. 2005, 9, 621.
3. Knorr, L. Ber. 1884, 17, 1635.
4. Knorr, L.; Lange, H. Ber. 1902, 35, 2998.
5. Eid, C. N.; Konopelski, J. P. Tetrahedron 1991, 47, 975.
6. Van Reymenant Chem. Zentralbl. 1901, 1, 72.
7. Henry Chem. Zentralbl. 1900, 1, 1123.
8. Levine, R.; Hauser, C. R. J. Am. Chem. Soc. 1946, 68, 760.
9. Hackler, R. E.; Burow, K. W.; Kaster, S. V.; Wickiser, D. I. J. Heterocycl. Chem. 1989, 26, 1575.
10. Eddington, N. D.; Cox, D. S.; Roberts, R. R.; Butcher, R. J.; Edafiogho, I. O.; Stables, J. P.; Cooke, N.; Goodwin, A. M.; Smith, C. A.; Scott, K. R. Eur. J. Med. Chem. Chim. Ther. 2002, 37, 635.
11. McFadden, H. G.; Huppatz, J. L. Aust. J. Chem. 1991, 44, 1263.
12. Claisen, L. Chem. Ber. 1903, 36, 3671.
13. Winans, C. F.; Adkins, H. J. Am. Chem. Soc. 1933, 55, 4167.
14. Chu, J. E.; Chu, T. C. J. Org. Chem. 1954, 19, 266.
15. Ehrhart, G. Chem. Ber. 1953, 86, 713, 716.
16. Fahmy, S. M.; Mohareb, R. M. Liebigs Ann. Chem. 1985, 7, 1492.
17. Castro, A. J.; Giannini, D. D.; Greenlee, W. F. J. Org. Chem. 1970, 35, 2815.
18. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry, 5th ed.; John Wiley & Sons, Inc.: 1989; p 1218.
19. Long, R. S. J. Am. Chem. Soc. 1947, 69, 990.