Synthesis and antimicrobial evaluation of 5-iodopyrimidine analogs

Abstract

4-Substituted-5-iodo-2-benzylthiopyrimidines were prepared efficiently in three steps. 2-Benzylthiopyrimidine on iodination in presence of base gave 5-iodo-2-benzylthiopyrimidine (1), which on chlorination with excess of POCl3 furnished 4-chloro-5-iodo-2-benzylthiopyrimidine (2). Reaction of 2 with substituted aromatic amines, 2-aminopyridine and hydrazine hydrate yielded 4-amino-5-iodo-2-benzylthiopyrimidines 3(a-e), (3f) and (3g) respectively. Further, 4-hydrazino-5-iodo-2-benzylthiopyrimidine on condensation with substituted aromatic and heterocyclic aldehydes afforded the corresponding schiff bases 4(a-h). The structure of synthesized compounds have been established by spectral studies and elemental analysis. Synthesized compounds have been screened for antimicrobial activity. Compound 3f exhibited good antifungal activity against A. niger. The compounds 4a, 4c, 4d, 4g and 4h exhibited good antibacterial activity.