Affiliation:
1. Riga Technical University
Abstract
Azetidine derivatives are interesting scaffolds in terms of medicinal chemistry. They can be regarded as structural homologs of aziridines. Herein we report synthetic approach to the novel N-protected 2-triazolyl azetidines which are structurally similar to our previously described aziridine derivatives with matrix metalloproteinase-2 inhihbitory activities. The synthetic rout includes ring closing of ethyl 2,4-dibromobutanoate, selective reduction of ester to aldehyde and transformation of the latter to terminal alkyne by Ohira-Bestmann reagent. 2-Ethynyl azetidines as key intermediates were transformed into triazole derivatives by Cu(I) catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction.
Publisher
Trans Tech Publications, Ltd.
Subject
Mechanical Engineering,Mechanics of Materials,General Materials Science
Cited by
1 articles.
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1. Four-Membered Ring Systems;Progress in Heterocyclic Chemistry;2020