Title: Carbodiimide mediated synthesis of new thiazolidin-4-ones and thiazinan-4-ones from thiosemicarbazone derivatives of 6,7-dihydro-1H-indazole-4(5H)-ones.
Authors: Gautam, Poonam; Chaudhary, Ram P.
Abstract: 5,5-Dimethyl-2-[(2-substitutedphenylhydrazinyl)methylene]cyclohexane-1,3-dione, obtained from heating dimedone with N,N′-dimethylformamide dimethyl acetal (DMF-DMA) and phenyl hydrazines, on cyclisation in ethanol gave 6,7-dihydro-1H-indazol-4(5H)-ones. The thiosemicarbazone derivative of 6,7-dihydro-1H-indazole-4(5H)-ones, on cyclocondensation with αand β-haloacids in the presence of N,N′-dicyclohexylcarbodiimide afforded new thiazolidin-4-ones and 1,3-thiazinan-4-ones respectively. Thiosemicarbazone of 6,7-dihydro-1H-indazol-4(5H)-ones on stirring with phenacyl bromides yields 2,4-disubstituted thiazoles. X-ray structure of the intermediate compound 5-dimethyl-2-[(2-phenylhydrazinyl)methylene] cyclohexane-1,3-dione was determined.
Subjects: CARBODIIMIDES; THIAZOLIDINEDIONES; ORGANONITROGEN compounds; RING formation (Chemistry); THIOSEMICARBAZONES; ORGANOSULFUR compounds
Publication: Journal of Chemical Research, 2014, Vol 38, Issue 4, p226
ISSN: 1747-5198
Publication type: Academic Journal
DOI: 10.3184/174751914X13940194215183

Carbodiimide mediated synthesis of new thiazolidin-4-ones and thiazinan-4-ones from thiosemicarbazone derivatives of 6,7-dihydro-1H-indazole-4(5H)-ones.

Gautam, Poonam; Chaudhary, Ram P.