A practical and inexpensive 'convertible' isonitrile for use in multicomponent reactions

Tetrahedron Letters

Volumn 52, Issue 17, 2011, Pages 2209-2211

  Le, Hoang V ^a   Fan, Lijun ^a   Ganem, Bruce ^a  

^a Department of Obstetrics Gynecology   (United States)

Author keywords

Amides to acids; Carboxyl protecting group; Combinatorial chemistry; Isonitrile based multicomponent reactions; t Butylisonitrile

Indexed keywords

BUTYLAMINE; CARBOXYLIC ACID; ISONITRILE DERIVATIVE;

ARTICLE; NITROSATION;

EID: 79953173901     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.156     Document Type: Article

References (22)

1. (a) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51;
2. (b) Dömling, A. Curr. Opin. Chem. Biol. 2000, 4, 318.
3. Mironov, M. A. QSAR Comb. Sci. 2006, 25, 423.
4. Elders, N.; van der Born, D.; Hendrickx, L.; Timmer, B.; Krause, A.; Janssen, E.; de Kanter, F.; Ruijter, E.; Orru, R. V. A. Angew. Chem., Int. Ed. 2009, 48, 5856.
5. (a) Dömling, A. Chem. Rev. 2006, 106, 17-89;
6. (b) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3169-3210.
7. Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1995, 117, 7842.
8. Lindhorst, T.; Bock, H.; Ugi, I. Tetrahedron 1999, 55, 7411.
9. Pirrung, M. C.; Ghorai, S. J. Am. Chem. Soc. 2006, 128, 11772.
10. (a) White, E. H. J. Am. Chem. Soc. 1955, 77, 6008;
11. (b) White, E. H. J. Am. Chem. Soc. 1955, 77, 60011.
12. Birney, D. M. Org. Lett. 2004, 6, 851.
13. (a) Nikolaides, N.; Ganem, B. J. Org. Chem. 1989, 54, 5996;
14. (b) Godfrey, A. G.; Ganem, B. J. Am. Chem. Soc. 1990, 112, 3717;
15. (c) Nikolaides, N.; Ganem, B. Tetrahedron Lett. 1990, 31, 1113;
16. (d) Nikolaides, N.; Godfrey, A. G.; Ganem, B. Tetrahedron Lett. 1990, 31, 6009.
17. (a) Lacey, R. N. J. Chem. Soc. 1960, 1633;
18. (b) Mahalingam, A. K.; Wu, X.; Alterman, M. Tetrahedron Lett. 2006, 3051;
19. (c) Takacs, E.; Varga, C.; Skoda-Foldes, R.; Kollar, L. Tetrahedron Lett. 2007, 48, 2453.
20. Kumar, J. S.; Jonnalagadda, S. C.; Mereddy, V. R. Tetrahedron Lett. 2010, 51, 779.
21. Romea, P.; Urpi, F.; Vilarrasa, J. J. Org. Chem. 1989, 54, 3209.
22. 9NC expedited with microwaves as a convertible isonitrile for heterocycle synthesis: Hulme, C.; Chappeta, S.; Dietrich, J. Tetrahedron Lett. 2009, 50, 4054.