Facile Syntheses of Some Thieno[2,3-d] Pyrimidine Derivatives

Abstract

In one-pot synthesis 2-arylidene-5,6,7,8-tetrahydrothiazolo[3,2-a] cyclopenteno-thieno[2,3-d] pyrimidine-3,5-diones (3) were prepared via the reaction of a ternary mixture of 2-thioxo-1,3,4,5,6,7-hexahydr cyclopentinothieno [2,3-d]-4-one (2), chloroacetic acid and a proper aldehyde. Compound 2 reacted with 3-chloropent-2, 4-dione in ethanolic potassium hydroxide yielding the S-acetyl acetone derivative 5f . The latter compound reacted with hydrazine hydrate and phenyl hydrazine yielded the 2-pyrazolthio derivative 10a, b. Compound 5f also underwent cyclization on heating with acetic acid—pyridine solution to give 11. The 2-methylthio derivative 5a, when treated with hydrogen peroxide gave the corresponding oxidized product 9.