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Mechanistic Studies on the Michael Addition of Amines and Hydrazines To Nitrostyrenes: Nitroalkane Elimination via a Retro-aza-Henry-Type Process

Michael G. Kallitsakis, Peter D. Tancini, Mudit Dixit, Giannis Mpourmpakis* and Ioannis N. Lykakis*

*Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece; University of Pittsburgh, Pittsburgh, Pennsylvania 15261, United States, Email: gmpourmppitt.edu, lykakischem.auth.gr

M. G. Kallitsakis, P. D. Tancini, M. Dixit, G. Mpourmpakis, I. N. Lykakis, J. Org. Chem., 2018, 83, 1176-1184.

DOI: 10.1021/acs.joc.7b02637 (free Supporting Information)


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Abstract

A Michael addition of amines and hydrazines to nitrostyrenes provides N-alkyl/aryl substituted benzyl imines and N-methyl/phenyl substituted benzyl hydrazones via a retro-aza-Henry-type process under mild, noncatalytic conditions. The method can be used for the synthesis of biologically important N-methyl pyrazoles in a one-pot manner, simple starting with the corresponding nitrostyrenes and the methylhydrazine.

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This protic solvent-mediated mechanism was proposed based on both experimental and theoretical studies.



Key Words

Imines, Hydrazones, Michael Addition, Henry Reaction


ID: J42-Y2018