Abstract
Recyclization of thieno[3,2-e][1,2,4]triazolo[4,3-c]pyrimidines was studied experimentally and theoretically by B3LYP/6-31G** calculations in the gas phase and in solution (EtOH). The experimentally observed characteristic features of the isomerization (the possibility of the Dimroth rearrangement occurring by the ANRORC mechanism and high energy barriers in acid-catalyzed reactions) were confirmed by quantum chemical calculations. Substituents in the triazole ring were found to play the principal role in the rearrangement.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2164–2171, December, 2006.
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Vorob’ev, E.V., Kletskii, M.E., Krasnikov, V.V. et al. Studies on mechanisms of the rearrangement of thieno[3,2-e][1,2,4]triazolo[4,3-c]pyrimidines into thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines. Russ Chem Bull 55, 2247–2255 (2006). https://doi.org/10.1007/s11172-006-0579-2
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DOI: https://doi.org/10.1007/s11172-006-0579-2