Please use this identifier to cite or link to this item: http://nopr.niscair.res.in/handle/123456789/14989
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 <b style="mso-bidi-font-weight:normal">1 </b>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 <b style="mso-bidi-font-weight:normal">2</b>.<b style="mso-bidi-font-weight: normal"> </b>Compound <b style="mso-bidi-font-weight:normal">2</b>, 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(1<i>H</i>)-one <b style="mso-bidi-font-weight:normal">3</b>. Further, compound <b style="mso-bidi-font-weight:normal">3</b>, on treatment with appropriate aldehydes, in ethanol give 6-methyl-4-phenyl-5-(5-{[(1<i>E</i>)-aryl­methyl­idene]amino}-1,3,4-oxadiazol-2-yl)-3,4-dihydropyrimidin-2(1<i>H</i>)-ones <b style="mso-bidi-font-weight:normal">4a-e</b>.<b style="mso-bidi-font-weight: normal"> </b>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(1<i>H</i>)-ones<b style="mso-bidi-font-weight:normal"> 5a-e </b>have been obtained by ring closure of the compounds <b style="mso-bidi-font-weight:normal">4a-e </b>with monochloroacetyl chloride in dioxane in the presence of triethylamine. The structures of the novel compounds are assigned based on IR, <sup>1</sup>H NMR, mass spectral data and elemental analysis data. All the compounds have been screened for their antimicrobial activity using bacterial and fungal strains.
Description: 1637-1641
URI: http://hdl.handle.net/123456789/14989
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.51B(11) [November 2012]

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