Synthesis and anti-cancer activity of pyridine and thiazolopyrimidine derivatives using 1-ethylpiperidone as a synthon

摘要

3,5-Bisarylmethylene-1-ethylpiperidone 2 on reaction with thiourea yield hte thioxopyrimidine derivatives 3,which on condensation with bromoacetic acid,2-bromopropanoic acid or 3-bromopropanoic acid afford thiazolopyrimidine 4,2-methyl-thiazolopyrimidines 5 and thiazinopyrimidine derivatives 6,respectively.Compounds 7 and 8 are also obtained via condensation of compounds 3 with 3-chloropentan-2,4-dione,bromoacetic acid and aromatic aldehydes,respectively.However,compounds 3 with 3-chloropentan-2,4-dione,bromoacetic acid and aromatic aldehydes,respectively.However,compounds 8 are prepared directly by condensation of compounds 4 with aromatic aldehydes. Compounds 2 on condensation with malononitrilein ethanol/piperidine or acetic acid/ammonium acetate mixture give pyridopyran 9 and pyridopyridine 10,respectively.Also compound 10 could be prepared directly from compoun9.Compounds 2 when condensed with phenylhydrazine,ethyl cyanoacetate or guanidine hydrochloride yields pyridopyrazole 11,pyridopyridone 12 and pyridoaminopyrimidine derivatives 13,respectively.