Synthesis of Triazoles via Regioselective Reactions of Aryl Azides with ­Cyanoacetyl Pyrroles and Indoles

Abstract

Novel 5-aminotriazoles are prepared by the cycloaddition reactions of aryl azides with cyanoacetyl pyrroles and indoles. The regioselectivity of these reactions is discussed.

Key words

triazoles - cycloadditions - regioselectivity - pyrroles - indoles­

References

• 1 Finley KT. Triazoles 1,2,3, In The Chemistry of Heterocyclic Compounds   Vol. 39:  Weissberger A. Taylor E. C. Wiley; New York: 1980.  p.1 
• 2 Fass RJ. Prior RB. Curr. Ther. Res.  1978,  24:  352 
• 3 Bohm R. Karow C. Pharmazie  1981,  36:  243 
• 4 Portmann R, Hofmeier UC, Burkhard A, Scherrer W, and Szelagiewicz M. inventors; WO  98/56773.  ; Chem. Abstr. 1999, 130, 57177
• 5 Alvarez R. Velazquez S. San-Felix A. Aquaro S. De Clercq E. Perno C.-F. Karlsson A. Balzarini J. Camarasa MJ. J. Med. Chem.  1994,  37:  4185 
• 6 Olesen PH. Sørensen AR. Ursø B. Kurtzhals P. Bowler AN. Ehrbar U. Hansen BF. J. Med. Chem.  2003,  46:  3333 
• 7 Bascal Z. Holden-Dye L. Willis RJ. Smith SWG. Walker RJ. Parasitology  1996,  112:  253 
• 8 Biagi G. Giorgi I. Livi O. Lucacchini A. Martini C. Scartoni V. J. Pharm. Sci.  1993,  82:  893 
• 9 Moltzen EK. Pedersen H. Bøgesø KP. Meier E. Frederiksen K. Sanchez C. Lembøl KL. J. Med. Chem.  1994,  37:  4085 
• 10 Chakrabarti JK. Hotten TM. Pullar IA. Steggles DJ. J. Med. Chem.  1989,  32:  2375 
• 11 Sanghvi YS. Bhattacharya BK. Kini GD. Matsumoto SS. Larson SB. Jolley WB. Robins RK. Revankar GR. J. Med. Chem.  1990,  33:  336 
• 12 Buckle DR. Rockell CJM. Smith H. Spicer BA. J. Med. Chem.  1986,  29:  2262 
• 13 Hupe DJ. Boltz R. Cohen CJ. Felix J. Ham E. Miller D. Soderman D. Van Skiver D. J. Biol. Chem.  1991,  266:  10136 
• 14 Krivopalov VP. Shkurko OP. Russ. Chem. Rev.  2005,  74:  339 
• 15 Cottrell IF. Hands D. Houghton PG. Humphrey GR. Wright SHB. J. Heterocycl. Chem.  1991,  28:  301 
• 16 Krivopalov VP. Nikolaenkova EB. Sedova VF. Mamaev VP. Chem. Heterocycl. Compd.  1983,  19:  1116 
• 17 Sundberg RJ. Indoles, In Best Synthetic Methods: Key Systems and Functional Groups   Meth-Cohn O. Academic Press; London: 1996. 
• 18 Slätt J. Romero I. Bergman J. Synthesis  2004,  2760