A Convenient Approach to 4,7‐Dihydrotetrazolo [5,1‐c][1,2,4]triazine Synthesis |
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| Authors: | Evgeny V. Shchegol'kov Anna E. Ivanova Yanina V. Burgart Viktor I. Saloutin |
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| Affiliation: | I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Sciences, , 620990 Ekaterinburg, Russian Federation |
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| 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. |
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