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Paper | Regular issue | Vol 68, No. 8, 2006, pp.1595-1605
Published online, 2nd June, 2006
DOI: 10.3987/COM-06-10760
Synthesis and Properties of Some Dihydrotetrazolo[5,1-c][1,2,4]triazines

Jalal A. Zahra, Mustafa M. El-Abadelah,* Bassam A. Abu Thaher, Naser S. El-Abadla, and Roland Boese

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

Abstract

(5-Mercaptotetrazol-1-yl)acetic acid - nitrile imine acyclic adducts (12a-c) undergo intramolecular cyclocondensation, induced by 1,1’-carbonyldiimidazole (CDI), to afford the respective dihydrotetrazolo[5,1-c][1,2,4]triazines (13a-c). The formation of the latter bicycles implies that 12a-c eject H2O and undergo S→N migration (Smiles rearrangement) with subsequent expulsion of O=C=S. The structures of 13a-c were determined by analytical and spectral data, and confirmed by single crystal X-Ray analysis for 13c.