Ma. Salama et Sa. El-essa, Synthesis and reactions of some new substituted phenylhydrazono ideno-thiazolo [3,2-b]pyrimidin-3-ones of possible antimicrobial activity, I J CHEM B, 40(8), 2001, pp. 678-681
Citations number
8
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY
3-Phenyl-hydrazono-1-indanone 1 on treatment with benzaldehyde gives 3-phen
yl-hydrazono-2-arylmethylene-indan-1 -ones 2a-d, which on reaction with thi
ourea in gl. acetic acid/Ac2O in the presence of anhyd. sodium acetate affo
rd 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-
aryI-5H-2,3-dihydro-6-phenyl-hydrazono-indeno[2',3'-blthiazolo[3,2-b]pyrimi
dine-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'-blthiazo
lo[3,2-b]pyrimidine-3-ones 5a-g. Compounds 5a-d are coupled with aryldiazon
ium salts in pyridine to give 2-aryl-hydrazon-5H-5-aryl-2,3-dihydro-6-pheny
l-hydrazono-indeno[2',3'-b]thiazolo[3,2-b]-pyrimidine-3-ones 6. Also, compo
und 3 when reacted with 2- or 3-bromopropionicacid afford 2-methyl-2,3-dihy
dro-5H-5-aryl-6-phenyl-hydrazono-indeno[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 antimicrobi
al activity against bacteria and fungi.