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

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• 作者：E. V. Vorob’ev ; M. E. Kletskii ; V. V. Krasnikov ; V. V. Mezheritskii and D. V. Steglenko
• 关键词：8 ; 9 ; 10 ; 11 ; tetrahydrobenzo[b]thieno[2 ; 3 ; e][1 ; 2 ; 4]triazolo[4 ; 3 ; c]pyrimidines ; Dimroth rearrangement ; quantum chemical calculations
• 刊名：Russian Chemical Bulletin
• 出版年：2006
• 出版时间：December, 2006
• 年：2006
• 卷：55
• 期：12
• 页码：2247-2255
• 全文大小：646 KB
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Chemistry
  Organic Chemistry
  Inorganic Chemistry
  Russian Library of Science
  
• 出版者：Springer New York
• ISSN：1573-9171

文摘

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.