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1,2-reduction of alpha,beta-unsaturated hydrazones using dimethylamine-borane/p-toluenesulfonic acid: an easy route to allyl hydrazines

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JournalTetrahedron
DatePublished - 23 Sep 2002
Issue number39
Volume58
Number of pages8
Pages (from-to)7925-7932
Original languageEnglish

Abstract

alpha,beta-Unsaturated hydrazones can be easily converted into N-allyl hydrazines by reaction with dimethylamine-borane/p-toluenesulfonic acid under mild reaction conditions. The reduction works well for N'-allyhydrazides but N'-allyl-N,N-dimethylhydrazines are rapidly reoxidised by air and so need to be manipulated under an inert atmosphere prior to M-acylation. Competitive conjugate reduction can also be observed and the regioselectivity of the dimethylamine-borane attack is determined by steric and/or electronic factors. The procedure is also effective for the C=N reduction of unconjugated hydrazones. (C) 2002 Elsevier Science Ltd. All rights reserved.

    Research areas

  • reduction, hygrazones, hydrazines, boron and compounds, DIELS-ALDER REACTIONS, CYCLIZATION, KETONES, REARRANGEMENT, 1-AZADIENES, REDUCTION, REAGENTS, ADDUCTS

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