A Convenient Approach to 4, 7‐Dihydrotetrazolo [5, 1‐c][1, 2, 4]triazine Synthesis. (4th March 2013)

• Record Type: Journal Article
• Authors: Shchegol'kov, Evgeny V.; Ivanova, Anna E.; Burgart, Yanina V.; Saloutin, Viktor I.
• Is Part Of: Journal of heterocyclic chemistry. Volume 50(2013)Supplement 1
• Page Start: E80
• Page End: E86
• Publication Date: 2013-03-04
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.1068
• Languages: English
• ISSNs: 0022-152X

Abstract

Abstract : 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. Abstract :