Synlett

A Metal-Free, Aqueous and General Route to 1, 5-Disubstituted-1, 2, 3-triazoles:'Reversed Regioisomeric'1, 3-Dipolar Cycloaddition of Azides and Vinyl Sulfones

S Dey, D Datta, T Pathak

Index: Dey, Santu; Datta, Dhrubajyoti; Pathak, Tanmaya Synlett, 2011 , # 17 p. 2521 - 2524

Full Text: HTML

Citation Number: 9

Abstract

Abstract A metal-free, vinyl sulfone-based synthesis of 1, 5-disubstituted-1, 2, 3-triazoles is reported for the first time. These triazoles are easily formed in a regioselective fashion by heating under reflux a mixture of a substituted vinyl sulfone and an organic azide 'on water'. This powerful and practical route has the potential to be exploited for the synthesis of complex 1, 5-disubstituted-1, 2, 3-triazoles.

Related Articles:

A Metal??Free Multicomponent Cascade Reaction for the Regiospecific Synthesis of 1, 5??Disubstituted 1, 2, 3??Triazoles

[Cheng, Guolin; Zeng, Xiaobao; Shen, Jinhai; Wang, Xuesong; Cui, Xiuling Angewandte Chemie - International Edition, 2013 , vol. 52, # 50 p. 13265 - 13268 Angew. Chem., 2013]

Direct synthesis of 1, 5-disubstituted-4-magnesio-1, 2, 3-triazoles, revisited

[Krasinski, Antoni; Fokin, Valery V.; Sharpless, K. Barry Organic Letters, 2004 , vol. 6, # 8 p. 1237 - 1240]

Ce (OTf) 3-catalyzed [3+ 2] cycloaddition of azides with nitroolefins: Regioselective synthesis of 1, 5-disubstituted 1, 2, 3-triazoles

[Wang, Ying-Chun; Xie, Yu-Yang; Qu, Hong-En; Wang, Heng-Shan; Pan, Ying-Ming; Huang, Fu-Ping Journal of Organic Chemistry, 2014 , vol. 79, # 10 p. 4463 - 4469]

Lewis Acid Mediated Fragmentation of Tetrazoles towards Triazoles

[El Kaim, Laurent; Grimaud, Laurence; Pravin, Patil European Journal of Organic Chemistry, 2013 , # 22 p. 4752 - 4755]

Lewis Acid Mediated Fragmentation of Tetrazoles towards Triazoles

[El Kaim, Laurent; Grimaud, Laurence; Pravin, Patil European Journal of Organic Chemistry, 2013 , # 22 p. 4752 - 4755]

More Articles...