Synthesis and reactions of some new substituted phenylhydrazono ideno-thiazolo [3,2-<i>b</i>] pyrimidin-3-ones of possible antimicrobial activity

678-6813-Phenyl-hydrazono-1-indanone 1 on treatment with benzaldehyde gives 3-phenyl-hydrazono-2-arylmethylene-indan-1-ones 2a-d, which on reaction with thiourea in gl. acetic acid/Ac2O in the presence of anhyd. sodium acetate afford 4-aryl-1,2,3,4-tetrahydro-5-phenyl -hydrazono- indeno[2',3'-b]pyrimidine-2-thiones 3a-d. Compounds 3a-d on reaction with chloroacetic acid furnish 5-aryl-5H-2,3-dihydro-6-phenyl-hydrazono-indeno[2',3'-b] thiazolo[3,2-b]pyrimidine-3-ones 4a-d.Compounds 4a-d on condensation with benzaldehyde yield 2-arylmethylene-5H,5-aryl-2,3-dihydro-6-phenyl-hydrazonoindeno[2',3'-b] thiazolo[3,2-b]pyrimidine-3-ones 5a-g. Compounds 5a-d are coupled with aryldiazonium salts in pyridine to give 2-aryl-hydrazon-5H-5-aryl-2,3-dihydro-6-phenyl-hydrazono-indeno[2',3'-b]thiazolo[3,2-b]-pyrimidine-3-ones 6. Also, compound 3 when reacted with 2- or 3-bromopropionicacid afford 2-methyl-2,3-dihydro-5H-5-aryl-6-phenyl-hydrazonoindeno [2',3'-b]-thiazolo[3,2-b]-pyrimidine-3-ones 7 and 6-aryl-6H-7-phenyl-hydrazono-indeno[2',3' -b] pyrimidino-[3,2-b]-1,3-thiazine-4-ones 8. Some of the compounds show considerable antimicrobial activity against bacteria and fungi