A new pyrrole synthesis via silver(I)-catalyzed cycloaddition of vinylogous diazoester and nitrile

Organic Letters

Volumn 15, Issue 7, 2013, Pages 1421-1423

  Billedeau, Roland J ^a   Klein, Klara R ^a   Kaplan, Daniel ^a   Lou, Yan ^a,b  

^a HOFFMANN LA ROCHE INC   (United States)

^b NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NITRILE; PYRROLE DERIVATIVE; SILVER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLOADDITION; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLOADDITION REACTION; MOLECULAR STRUCTURE; NITRILES; PYRROLES; SILVER;

EID: 84875939930     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400062w     Document Type: Article

References (26)

1. Hou, X. L.; Yang, Z.; Wong, H. N. C. In Progress in Heterocyclic Chemistry; Gribble, G. W., Gilcrist, T. L., Eds; Pergamon: Oxford, 2003; Vol. 15, p 167.
2. Boger, D. L.; Boyce, C. W.; Labrili, M. A.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 54
3. Muchowski, J. M. Adv. Med. Chem. 1992, 1, 109
4. Knorr, L. Chem. Ber 1884, 17, 1635
5. Bergman, J.; Janosik, T. Modern Heterocyclic Chemistry 2011, 1, 269
6. Joule, J. A.; Mills, K. Heterocyclic Chemistry; Blackwell Science: Oxford, U.K., 2000; Chapter 13.
7. Balme, G. Angew. Chem., Int. Ed. 2004, 43, 6238
8. Qi, X.; Xu, X.; Park, C.-M. Chem. Commun. 2012, 48, 3996
9. Bauer, I.; Knölker, H.-J. Top. Curr. Chem. 2012, 309, 203
10. Estevez, V.; Villacarpa, M.; Menendez, J. C. Chem. Soc. Rev. 2010, 39, 4402
11. Wang, H.-Y.; Mueller, D. S.; Sachwani, R. M.; Kapadia, R.; Londino, H. N.; Anderson, L. L. J. Org. Chem. 2011, 76, 3203
12. Yamamoto, H.; Sasaki, I.; Mitsutake, M.; Karasudani, A.; Imagawa, H.; Nishizawa, M. Synlett 2011, 19, 2815
13. Patil, N. T.; Yamamoto, Y. ARKIVOC 2007, 121
14. Dudnik, A. S.; Scromek, A. W.; Rubina, M.; Kim, J. T.; Kel'in, A. V.; Gevorgyan, V. J. Am. Chem. Soc. 2008, 130, 1440
15. Chen, F.; Shen, T.; Cui, Y.; Jiao, N. Org. Lett. 2012, 14, 4926
16. Zhang, Y.; Zhang, J. Synlett 2012, 23, 1389
17. Kim, J. H.; Lee, S. B.; Lee, W. K.; Yoon, D.-H.; Ha, H.-J. Tetrahedron 2011, 67, 3553
18. Liu, W.; Jiang, H.; Huang, L. Org. Lett. 2010, 12, 312
19. Dong, H.; Shen, M.; Redford, J. E.; Stokes, B. J.; Pumphrey, A. L.; Driver, T. G. Org. Lett. 2007, 9, 5191
20. Gabriele, B.; Salerno, G.; Fazio, A. J. Org. Chem. 2003, 68, 7853
21. Doyle, K. J.; Moody, C. J. Tetrahedron 1994, 50, 3761
22. Ye, T.; Mckervey, M. A. Chem. Rev. 1994, 94, 1091
23. Zhang, Z.; Wang, J. Tetrahedron 2008, 64, 6577
24. Gant, T. G.; Noe, M. C.; Corey, E. J. Tetrahedron Lett. 1995, 36, 8745
25. Thompson, J.; Davies, H. M. L. J. Am. Chem. Soc. 2007, 129, 6090
26. Briones, J. F.; Davies, H. M. L. Org. Lett. 2011, 13, 3984