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Synthesis and Some Transformations of 4-Oxo-7-phenyl-3,4,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidine-7-carbonitrile

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Abstract

The condensation of ethyl 2-amino-6-cyano-6-phenyl-4,5,6,7-tetrahydro-1-benzothiophene-3-car­boxylate with formamide gave 4-oxo-7-phenyl-3,4,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidine-7-carbo­nitrile which was treated with phosphoryl chloride to obtain the corresponding 4-chloro derivative. Reactions of the latter with secondary amines afforded a series of 4-aminobenzothienopyrimidines, and the reaction with hydrazine hydrate, followed by cyclization with formic acid, furnished 9-phenyl-8,9,10,11-tetrahydro[1]benzothieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-9-carbonitrile.

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Authors and Affiliations

  1. Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, 0014, Yerevan, Armenia

    А. А. Aghekyan, G. G. Mkryan, H. A. Panosyan, A. S. Grigoryan & H. V. Gasparyan

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  1. А. А. Aghekyan
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  2. G. G. Mkryan
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  3. H. A. Panosyan
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  4. A. S. Grigoryan
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  5. H. V. Gasparyan
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Correspondence to А. А. Aghekyan.

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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 10, pp. 1451–1456 https://doi.org/10.31857/S0514749221100116.

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Aghekyan, А.А., Mkryan, G.G., Panosyan, H.A. et al. Synthesis and Some Transformations of 4-Oxo-7-phenyl-3,4,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidine-7-carbonitrile. Russ J Org Chem 57, 1638–1642 (2021). https://doi.org/10.1134/S1070428021100110

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  • DOI: https://doi.org/10.1134/S1070428021100110

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