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Keywords:

  • one-pot reaction;
  • domino reaction;
  • electron-deficient alkyne;
  • thiourea;
  • pyrimidin-2-thione

Abstract

In the presence of zinc chloride, the in situ generated β-enamino ester from the reaction of morpholine, piperidine and pyrrolidine with methyl propiolate reacted, with aromatic aldehydes and thiourea in ethanol resulting in the functionalized tetrahydropyrimidin-2-thiones in satisfactory yields and with good diastereoselectivity. When aromatic aldehydes bearing electron-withdrawing group were used in the reaction, the 4-hydroxytetrahydropyrimidin-2-thione derivatives were obtained as the main product.