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Short Paper | Regular issue | Vol 85, No. 7, 2012, pp.1727-1733
Published online, 6th June, 2012
DOI: 10.3987/COM-12-12516
Double Intramolecular 1,3-Dipolar Cycloaddition of Diazo-terminal Dialkyne: Synthesis of a New Bis(1,2,3-triazolo-1,4-oxazine)

Mekni Husein Nejib* and Ahmed Baklouti

*Department of Chemistry, Faculty of Scince, University of Tunis, Almanar, 2092 Tunis, Tunisia

Abstract

A new bis(1,2,3-triazolo-1,4-oxazine) fused heterocyclic compound was synthesized from terminal meso-1,2,3,4-diepoxybutane via azide ring opening reaction, followed by propargylation and double 1,3-dipolar intramolecular cycloaddition. No effect on the reaction outcome was observed when Cu(I) was used as catalyst. In both cases catalyzed and uncatalyzed reactions, only the exo-tetracyclic two to two fused isomer was obtained.