The synthesis of 3-(het)aryl-6,7-dihydro-5H-[1,2,4]-triazolo[3,4-a][2]benzazepines

4-Aryl-2-methylbutan-2-ols with methoxy or methylenedioxy substituents participate in the Graf–Ritter reaction with methyl thiocyanate in the presence of an acid (H2SO4, MeSO3H) forming 1-methylsulfanyl-2-benzazepines in low yields (11–35%), which undergo cyclization with benzhydrazide or hetarenecarboxylic acid hydrazides upon reflux in o-dichlorobenzene into the corresponding 3-phenyl- and 3-hetaryl-6,7-dihydro-5H-1,2,4-triazolo[3,4-a][2]benzazepines (45–74% yields).

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The work was carried out in accordance with State assignment No. AAA-A18-118030790037-7 using equipment from the Center for Collective Use “ Research of Materials and Substances” of the Perm Federal Research Center of the Ural Branch of the Russian Academy of Sciences.

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Correspondence to Vladimir А. Glushkov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(1), 63–68

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Glushkov, V.А., Babentsev, D.N., Dmitriev, M.V. et al. The synthesis of 3-(het)aryl-6,7-dihydro-5H-[1,2,4]-triazolo[3,4-a][2]benzazepines. Chem Heterocycl Comp 57, 63–68 (2021). https://doi.org/10.1007/s10593-021-02868-9

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Keywords

  • 4-aryl-2-methylbutan-2-ols
  • benz[c]azepines
  • hetarenecarboxylic acid hydrazides
  • methyl thiocyanate
  • 1,2,4-triazolo-2-benzazepines
  • Ritter reaction