Abstract <p>Methods of synthesis of new fused thieno[3,2-<i>e</i>]pyridines and thieno[3,2-<i>d</i>]pyrimidines have been developed. 4-(Furan-2-yl)-7,7-dimethyl-2-sulfanyl-7,8-dihydro-5<i>H</i>-pyrano[4,3-<i>b</i>]pyridine-3-carbonitrile has been found to react with 2-chloroacetamides in two directions, depending on the temperature. The reaction at elevated temperature (60–65°C) involved alkylation followed by intramolecular cyclization with the formation of pyrano[4,3-<i>b</i>]thieno[3,2-<i>e</i>]pyridine derivatives, whereas at room temperature, the corresponding 2-sulfanyl­acetamides were obtained. The condensation of pyrano[4,3-<i>b</i>]thieno[3,2-<i>e</i>]pyridine-2-carboxamides with triethyl orthoformate afforded new fused tetracyclic thieno[3,2-<i>d</i>]pyrimidine derivatives.</p>

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Synthesis of New Fused Thieno[3,2-d]pyrimidine Derivatives Based on 4-(Furan-2-yl)-7,7-dimethyl-2-sulfanyl-7,8-dihydro-5H-pyrano[4,3-b]pyridine-3-carbonitrile

  • V. V. Dabayeva,
  • I. M. Barkhudaryants,
  • E. G. Paronikyan,
  • Sh. Sh. Dashyan,
  • M. R. Baghdasaryan

摘要

Abstract

Methods of synthesis of new fused thieno[3,2-e]pyridines and thieno[3,2-d]pyrimidines have been developed. 4-(Furan-2-yl)-7,7-dimethyl-2-sulfanyl-7,8-dihydro-5H-pyrano[4,3-b]pyridine-3-carbonitrile has been found to react with 2-chloroacetamides in two directions, depending on the temperature. The reaction at elevated temperature (60–65°C) involved alkylation followed by intramolecular cyclization with the formation of pyrano[4,3-b]thieno[3,2-e]pyridine derivatives, whereas at room temperature, the corresponding 2-sulfanyl­acetamides were obtained. The condensation of pyrano[4,3-b]thieno[3,2-e]pyridine-2-carboxamides with triethyl orthoformate afforded new fused tetracyclic thieno[3,2-d]pyrimidine derivatives.