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Regiospecific Aza-Michael Addition of 4-Aryl-1H-1,2,3-triazoles to Chalcones: Synthesis of 2,4-Disubstituted 1,2,3-Triazoles in Basic Medium.

Authors :
Bhagat, Ujjawal Kumar
Peddinti, Rama Krishna
Source :
Synlett. 2018, Vol. 29 Issue 1, p99-105. 7p. 4 Diagrams, 2 Charts.
Publication Year :
2018

Abstract

A novel metal-free and base-mediated method to display the donor ability of 1,2,3-triazoles for the synthesis of 2,4-disubstituted 1,2,3-triazoles has been developed. A DABCO-promoted aza-Michael addition of 4-aryl NH-1,2,3-triazoles to α,β-unsaturated ketones (chalcones) is presented. The reactions proceeded with complete regiospecificity in a 3:1 mixture of acetonitrile and methanol at 85 °C to provide 2,4-disubstituted 1,2,3-triazoles as Michael adducts, and the addition products 1,3-diaryl-(4-aryl-2H-1,2,3-triazol-2-yl)propan-1-ones were isolated in high yields. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
09365214
Volume :
29
Issue :
1
Database :
Academic Search Index
Journal :
Synlett
Publication Type :
Academic Journal
Accession number :
126846597
Full Text :
https://doi.org/10.1055/s-0036-1588567