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Paper | Regular issue | Vol 36, No. 3, 1993, pp.455-472
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6096
Ring Transformations of Heterocycles 2. Ring Contraction of 5,6-Dihydro-4H-1,2,4,5-oxatriazines into 1H-1,2,4-Triazoles

Mustafa M. El-Abadelah,* Ahmad Q. Hussein, Musa Z. Nazer, Osama M. Musa, Paul Rademacher,* and Heinz Bandmann

*Chemistry Department, Faculty of Science, University of Jordan, Amman 11942, Jordan

Abstract

6-Monosubstituted 5,6-dihydro-4H-1,2,4,5-oxatriazines (3) undergo ring contraction, via elimination of H2O, to yield the respective 1H-1,2,4-triazoles (4). This transformation is envisaged to proceed via the ring-opened (E)-hydrazonoxime (5) which then suffers dehydrative cyclization. The process is acid-catalyzed and is thermally induced. Apparently, the driving force for this transformation is linked to the aromaticity of the triazole product.