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Synthesis of 5,8-Diamino-Substituted Pyrano[4″,3″:4′,5′]pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidines and Pyrimido[4′,5′:4,5]thieno[2,3-c]isoquinolines

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Abstract

Ethyl 1-amino-8,8-dimethyl-5-(piperidin-1-yl)-8,9-dihydro-6H-pyrano[4,3-d]thieno[2,3-b]pyridine-2-carboxylate and ethyl 1-amino-5-(piperidin-1-yl)-6,7,8,9-tetrahydrothieno[2,3-c]isoquinoline-2-carboxylate reacted with benzoyl isothiocyanate to give the corresponding 1-thioureido derivatives which underwent cyclization to 2,2-dimethyl-5-(piperidin-1-yl)-10-thioxo-1,4,10,11-tetrahydro-2H-pyrano[4″,3″:4′,5′]pyrido-[3′,2′:4,5]thieno[3,2-d]pyrimidin-8(9H)-one and 5-(piperidin-1-yl)-10-thioxo-1,2,3,4,10,11-hexahydropyrimido-[4′,5′:4,5]thieno[2,3-c]isoquinolin-8(9H)-one. The cyclization products were converted into 8-chloro derivatives, and the chlorine atom therein was replaced by various amines.

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Authors and Affiliations

  1. Mndzhoyan Institute of Fine Organic Chemistry, Scientific and Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, pr. Azatutyan 26, Yerevan, 0014, Armenia

    E. G. Paronikyan, Sh. Sh. Dashyan & G. M. Stepanyan

  2. Molecular Structure Research Center, Scientific and Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, pr. Azatutyan 26, Yerevan, 0014, Armenia

    N. S. Minasyan

Authors
  1. E. G. Paronikyan
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  2. Sh. Sh. Dashyan
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  3. N. S. Minasyan
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  4. G. M. Stepanyan
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Correspondence to Sh. Sh. Dashyan.

Additional information

Original Russian Text © E.G. Paronikyan, Sh.Sh. Dashyan, N.S. Minasyan, G.M. Stepanyan, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 4, pp. 589–593.

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Paronikyan, E.G., Dashyan, S.S., Minasyan, N.S. et al. Synthesis of 5,8-Diamino-Substituted Pyrano[4″,3″:4′,5′]pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidines and Pyrimido[4′,5′:4,5]thieno[2,3-c]isoquinolines. Russ J Org Chem 52, 576–581 (2016). https://doi.org/10.1134/S1070428016040187

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  • DOI: https://doi.org/10.1134/S1070428016040187

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