A Convenient Approach to 4,7-Dihydrotetrazolo [5,1-c][1,2,4]triazine Synthesis

作者:Shchegol'kov Evgeny V*; Ivanova Anna E; Burgart Yanina V; Saloutin Viktor I
来源:Journal of Heterocyclic Chemistry, 2013, 50(S1): E80-E86.
DOI:10.1002/jhet.1068

摘要

Azo coupling of 1,3-dicarbonyl compounds with tetrazolyl-5-diazonium chloride is used to develop a convenient one-step procedure for the synthesis of 4,7-dihydrotetrazolo[5,1-c][1,2,4]triazines. In contrast to nonfluorinated analogs, 7-hydroxy-7-polyfluoroalkyl-4,7-dihydrotetrazolo[5,1-c][1,2,4]triazines undergo a ring-chain isomerism resulting from the cleavage at the C7?N7a bond. A distinctive feature of nonfluorinated 4,7-dihydrotetrazolo[5,1-c][1,2,4]triazines is the possibility to dehydration, which is accompanied by an azide rearrangement due to the tetrazole ring cleavage with the formation of tetrazolo[1,5-b][1,2,4]triazines.

  • 出版日期2013-2