Synlett
DOI: 10.1055/s-0036-1588567
letter
© Georg Thieme Verlag Stuttgart · New York

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

Ujjawal Kumar Bhagat, Rama Krishna Peddinti*
U.K.B. gratefully thanks to Ministry of Human Resource Development, New Delhi, India for providing a fellowship.
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Publication History

Received: 22 July 2017

Accepted after revision: 19 August 2017

Publication Date:
14 September 2017 (eFirst)

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.

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