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Synthesis 2020; 52(09): 1379-1386
DOI: 10.1055/s-0039-1691591
DOI: 10.1055/s-0039-1691591
paper
Copper-Catalyzed Tandem Dehydrocyanation and [3+2] Cycloaddition Reactions of Phenacylmalononitriles: Regioselective Synthesis of Functionalized 4-Benzoyl-5-cyanopyrazoles under Mild Conditions
We are grateful to the Research Council of Tarbiat Modares University for support of this work.Further Information
Publication History
Received: 14 November 2019
Accepted after revision: 14 January 2020
Publication Date:
06 February 2020 (online)
Abstract
A novel copper-catalyzed [3+2] cycloaddition reaction with concomitant in situ generation of benzoylacrylonitriles and nitrile imines from phenacylmalononitriles and hydrazonoyl chlorides, respectively, is reported. The reaction was performed using copper(I) chloride as catalyst and N-methylimidazole as a clean complexing agent/weak base to afford the functionalized 4-benzoyl-5-cyanopyrazoles in moderate to good yields and excellent regioselectivity under ambient conditions. This method provides rapid access to a wide range of highly functionalized 4-benzoyl-5-cyanopyrazoles.
Key words
4-benzoyl-5-cyanopyrazoles - copper catalysis - [3+2] cycloaddition - phenacylmalononitrile - hydrazonoyl chlorideSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1691591.
- Supporting Information
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See, for example: