The First Multicomponent Synthesis of Propargyl-1,2,3-triazoles [¹]

Abstract

The three-component reaction of benzotriazoles, aldehydes, and alkynes has been carried out for the first time using zinc bromide as a catalyst. The corresponding propargylbenzotriazoles are formed in high yields (79-97%) within 6-10 hours.

Key words

propargyl-1,2,3-triazole - benzotriazole - aldehyde - alkyne - zinc bromide

1

Part 209 in the series ‘Studies on Novel Synthetic Methodologies.’

References

• 2a Chabre YM. Roy R. Curr. Top. Med. Chem.  2008,  8:  1237 
• 2b Moumne R. Larue V. Seijo B. Lecourt T. Micouin L. Tisne C. Org. Biomol. Chem.  2010,  8:  1154 
• 3 Meldal M. Tornoe CW. Chem. Rev.  2008,  108:  2952 
• 4a Wender PA. Touami SM. Alayrac C. Philipp UC. J. Am. Chem. Soc.  1996,  118:  6522 
• 4b Baragatte B. Biagi G. Calderone V. Giorgi I. Livi O. Martinotti E. Scartoni V. Eur. J. Med. Chem.  2000,  35:  949 
• 5a Rozkiewicz DI. Janezewski D. Verboom W. Ravoo BJ. Reinhoudt DN. Angew. Chem. Int. Ed.  2006,  45:  5293 
• 5b Golas PL. Matyjaszewski K. Chem. Soc. Rev.  2010,  39:  1338 
• 6a Fazio MA. Lee OP. Schuster DI. Org. Lett.  2008,  10:  4979 
• 6b Hua YR. Flood AH. Chem. Soc. Rev.  2010,  39:  1262 
• 7 Duan H. Sengupta S. Petersen JL. Akhmedov NG. Shi X. J. Am. Chem. Soc.  2009,  131:  12100 
• 8 Stang PJ. Diederich F. Modern Acetylene Chemistry   VCH; Weinheim: 1995. 
• 9a Das B. Reddy GC. Balasubramanyum P. Salvanna N. Synthesis  2011,  816 
• 9b Das B. Reddy ChR. Sindhu Ch. Kumar DN. Krishnaiah M. Helv. Chim. Acta  2011,  94:  289 
• 10a Armstrong RW. Combs AP. Tempest PA. Brown SD. Keating TA. Acc. Chem. Res.  1996,  29:  123 
• 10b Dömling A. Ugi I. Angew. Chem. Int. Ed.  2000,  39:  3168 
• 10c Estevez V. Villacampa M. Menendez JC. Chem. Soc. Rev.  2010,  39:  4402 
• 11 Yan W. Wang Q. Chen Y. Peterson JL. Shi X. Org. Lett.  2010,  12:  3308 
• 12 Fischer C. Carreira EM. Org. Lett.  2004,  6:  1497 

1

Part 209 in the series ‘Studies on Novel Synthetic Methodologies.’