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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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| Journal | Tetrahedron |
|---|---|
| Date | Published - 23 Sep 2002 |
| Issue number | 39 |
| Volume | 58 |
| Number of pages | 8 |
| Pages (from-to) | 7925-7932 |
| Original language | English |
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.
- reduction, hygrazones, hydrazines, boron and compounds, DIELS-ALDER REACTIONS, CYCLIZATION, KETONES, REARRANGEMENT, 1-AZADIENES, REDUCTION, REAGENTS, ADDUCTS
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