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Paper | Special issue | Vol 67, No. 2, 2006, pp.749-762
Published online, 30th September, 2005
DOI: 10.3987/COM-05-S(T)77
Synthesis of 5-Selenoxo-1,2,4-triazole-1-carboxylates from Isoselenocyanates and Azodicarboxylates

Francesco Favero, Geoffroy L. Sommen, Anthony Linden, and Heinz Heimgartner*

*Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland

Abstract

A mixture of an azodicarboxylate and triphenylphosphine in dichloromethane reacted with aryl isoselenocyanates (1) at room temperature to give 4,5-dihydro-5-selenoxo-1H-1,2,4-triazole-1-carboxylates (4a-f) in a one-pot reaction in good to excellent yields. The isoselenocyanates (1) have been prepared conveniently from formamides by treatment with elemental selenium and phosgene according to Barton’s procedure.