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Synthesis 2008(20): 3295-3298  
DOI: 10.1055/s-0028-1083142
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Solvent-Free Synthesis of Hydrazine-Substituted Enaminones via a One-Pot Four-Component Reaction

Abdolali Alizadeh*, Mohadeseh Babaki, Nasrin Zohreh
Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran 18716, Iran
Fax: +98(21)88006544; e-Mail: abdol_alizad@yahoo.com; e-Mail: aalizadeh@modares.ac.ir;
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Publication History

Received 2 June 2008
Publication Date:
25 September 2008 (online)

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Abstract

A four-component reaction for the synthesis of hydrazine-substituted enaminones is illustrated. In situ generation of a β-keto ester or β-keto amide from diketene and ROH or RNH2 and then reaction with a primary amine to produce enaminones, followed by functionalization of the adduct by C-N bond formation through reaction with diisopropyl diazodicarboxylate, are performed under solvent-free conditions in one pot to obtain the title compound in good yield.

Key words

diketene - diisopropyl diazodicarboxylate - four-component reaction - solvent-free reaction - hydrazine - enamine, enaminone

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