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Title: Synthesis and antimicrobial activity studies of certain pyrimidinyl oxadiazolo azetidinones
Authors: George, Sonia
Sabitha, R
Govindhammal, V
Ravi, T K
Keywords: Pyrimidinyl oxadiazoles;Azetidinones;Antibacterial activity;Antifungal activity
Issue Date: Nov-2012
Publisher: NISCAIR-CSIR, India
Abstract:   Aryl substituted pyrimidinyl oxadiazolo azetidinones have been synthesized from ethyl 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate 1 which on reaction with semicarbazide hydrochloride in ethanol yields 2-[(6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidin-5-yl)carbonyl]hydra­zi­ne­carboxamide 2. Compound 2, on reaction with concentrated sulphuric acid, undergo cyclization to yield 5-(5-amino-1,3,4-oxadiazol-2-yl)-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one 3. Further, compound 3, on treatment with appropriate aldehydes, in ethanol give 6-methyl-4-phenyl-5-(5-{[(1E)-aryl­methyl­idene]amino}-1,3,4-oxadiazol-2-yl)-3,4-dihydropyrimidin-2(1H)-ones 4a-e. Finally, the title compounds 5-[5-(3-chloro-2-oxo-4-arylazetidin-1-yl)-1,3,4-oxadiazol-2-yl]-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-ones 5a-e have been obtained by ring closure of the compounds 4a-e with monochloroacetyl chloride in dioxane in the presence of triethylamine. The structures of the novel compounds are assigned based on IR, 1H NMR, mass spectral data and elemental analysis data. All the compounds have been screened for their antimicrobial activity using bacterial and fungal strains.
Page(s): 1637-1641
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.51B(11) [November 2012]

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