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Synthesis and Antimicrobial Activity of New 2-Azetidinones from N-(Salicylidene) Amines and 2-Diazo-1, 2-Diarylethanones

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dc.creator Singh, Girija S.
dc.creator Mbukwa, Elbert A.
dc.creator Pheko, Tshepo
dc.date 2016-06-15T20:53:30Z
dc.date 2016-06-15T20:53:30Z
dc.date 2007
dc.date.accessioned 2018-03-27T08:54:31Z
dc.date.available 2018-03-27T08:54:31Z
dc.identifier Singh, G.S., Mbukwa, E. and Pheko, T., 2007. Synthesis and antimicrobial activity of new 2-azetidinones from N-(salicylidene) amines and 2-diazo-1, 2-diarylethanones. Arkivoc, 9, pp.80-90.
dc.identifier 1424-6376
dc.identifier http://hdl.handle.net/20.500.11810/2482
dc.identifier.uri http://hdl.handle.net/20.500.11810/2482
dc.description This paper describes the reactions of N-salicylideneamines with diarylketenes generated from thermal decomposition of the 2-diazo-1,2- diarylethanones. An equimolar reaction of the N-salicylidenebenzhydrylamine with diphenylketene affords a mixture of 2-[(benzhydrylimino)methyl]phenyl-2,2- diphenylacetate as a major product and 1-benzhydryl-3,3-diphenyl-4-[2′-(O- diphenylacyl)hydroxyphenyl]-2-azetidinone as a minor product. The reactions of various N-salicylideneamines with 2.2 molar equivalents of 2-diazo-1,2- diarylethanones have been carried out to afford 1-substituted-3,3-diaryl-4- [2′-(O-diarylacyl)hydroxyphenyl]-2-azetidinones as sole product in excellent yields. The products, characterized on the basis of satisfactory analytical and spectral data, have shown moderate to good antimicrobial activity against some bacteria and fungi. Among the fourteen compounds in the series, the 2-azetidinone 4l with a 4-chlorophenyl group on β-lactam ring nitrogen and 4-methylphenyl groups on β-lactam ring C-3 position is the most active compound.
dc.language en
dc.subject 2-Azetidinones
dc.subject Diarylketenes
dc.subject Iminophenols
dc.subject Cycloaddition
dc.subject Antimicrobial
dc.title Synthesis and Antimicrobial Activity of New 2-Azetidinones from N-(Salicylidene) Amines and 2-Diazo-1, 2-Diarylethanones
dc.type Journal Article, Peer Reviewed


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