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Short Paper | Regular issue | Vol 87, No. 8, 2013, pp.1765-1773
Published online, 27th June, 2013
DOI: 10.3987/COM-13-12752
Three-Step Synthesis of Triazolobenzodiazepinones via Sonogashira/Huisgen Protocol

Giorgio Molteni*

*Department of Organic and Industrial Chemistry, University of Milano, Via Golgi 19, 20133 Milano, Italy

Abstract

The sequential Sonogashira coupling/intramolecular azide cycloaddition (Huisgen cycloaddition) protocol was performed onto N-(2-iodophenyl)-2-azidoacetamide as the acyclic precursor giving tricyclic 1,2,3-triazolo[5,1-d][1,4]benzodiazepin-2-ones. These target products were thus obtained through a three-step synthesis in variable yields depending upon the substituent placed onto the acetylenic counterpart. The influence of catalyst concentration, reaction temperature and reaction medium upon cycloadduct yields were also studied.