Potential anticancer drugs: synthesis of some fused arylhydrazonoindeno [1,2-d] thiazolo and thiazinopyrimidinones

ABSTRACT

4-aryl-1,2,3,4-tetrahydro-5-oxoindeno [1,2-d] pyrimidine-2-thiols [I] were synthesized in the laboratories and their corresponding hydrazono derivatives [II] were submitted to react with chloroacetic acid, 2-bromopropionic acid or 3-bromopropionic acid in the presence of fused sodium acetate and acetic anhydride to give 5-aryl-2,3- dihydro-5H, 6-arylhydrazonoindeno [1,2-d] thiazolo [3,2-a] pyrimidin-3-ones [III], its methyl derivatives [IV] and 6-aryl-6H, 7-arylhydrazonoindeno [1,2-d]-pyrimidino-[2,1-b]-1,3-thiazin-4-ones [V], respectively. The indenothiazolopyrimidones [III] condensed with aromatic aldehydes in the presence of acetic anhydride to yield 2-arylmethylene-5 aryl-2,3-dihydro-5H-6-arylhydrazonoimdeno [1,2-d] thiazolo [3,2-a] pyrimidin-3-ones [VI], which was obtained directly from their arylhydrazono derivatives [II] by the reaction of chloroacetic acid in the presence of the corresponding aromatic aldehyde and in refluxing acetic acid/acetic anhydride mixture