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Fused Diazepines. Synthesis of 2-Methyl-8-aryl-4,6-dihydro-5H-thieno[3',2':4,5]thieno[2,3-d][1,2]diazepin-5-ones

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Abstract

Heterocyclization of ethyl 2-acetyl(aroyl)-5-methylthieno[2,3-b]thiophene-3-acetates with hydrazine hydrate has been studied. A dependence of the reaction direaction on the nature of the substituent in the acyl fragment was established. The heterocyclization of ethyl 2-aroyl-5-methylthieno[2,3-b]thiophene-3-acetates leads to derivatives of thieno[3',2':4,5]thieno[2,3-d][1,2]diazepin-5-ones. The cyclization of ethyl 2-acetyl-5-methylthieno[2,3-b]thiophene-3-acetate with hydrazine hydrate forms a six-membered ring, viz. 2-aminothieno[3',2':4,5]thieno[2,3-c]pyridin-5(6H)-one.

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Authors and Affiliations

  1. Litvinenko Institute of Physical Organic and Coal Chemistry, 83114, Donetsk, Ukraine

    A. V. Muratov & A. B. Eresko

  2. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, 02160, Kiev, Ukraine

    V. S. Tolkunov & S. V. Tolkunov

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  1. A. V. Muratov
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  2. A. B. Eresko
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  3. V. S. Tolkunov
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  4. S. V. Tolkunov
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Correspondence to A. B. Eresko.

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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 2, pp. 212–218 https://doi.org/10.31857/S0514749221020075.

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Muratov, A.V., Eresko, A.B., Tolkunov, V.S. et al. Fused Diazepines. Synthesis of 2-Methyl-8-aryl-4,6-dihydro-5H-thieno[3',2':4,5]thieno[2,3-d][1,2]diazepin-5-ones. Russ J Org Chem 57, 180–185 (2021). https://doi.org/10.1134/S107042802102007X

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