Synthesis of 1-alkynyl-2-dialkylaminocyclopropanes and 1-alkynyl-2-diazolylcyclopropanes by reactions of 1-alkynyl-1-chlorocyclopropanes with amines and their lithium derivatives

Author: Shavrin K.   Gvozdev V.   Nefedov O.  

Publisher: Springer Publishing Company

ISSN: 1066-5285

Source: Russian Chemical Bulletin, Vol.59, Iss.2, 2010-02, pp. : 396-404

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Abstract

Reactions of 1-alkynyl-1-chlorocyclopropanes with lithium dialkylamides gave previously unknown 1-alkynyl-2-dialkylaminocyclopropanes. 1-(Alk-1-ynyl)-2-diazolylcyclopropanes were obtained by reactions of 1-alkynyl-1-chlorocyclopropanes with diazoles in the presence of KOH in DMSO at 100 °C. These reactions passed through the formation of conjugated alky-nylcyclopropenes and reversible addition of amide anions to them. The regioselectivity and stereoselectivity of these transformations depend on the substituents in the starting chlorocyclopropanes and amines.

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