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Syntheses of n substituted 3 3 4 tri phenyl 4 benzoyl azetidin 2 ones and 3' 3' di phenyl spiro acenaphthen 1 one 2 4' azetidin 2' ones novel examples exhibiting a high reactivity of imino group in ketimines



Syntheses of n substituted 3 3 4 tri phenyl 4 benzoyl azetidin 2 ones and 3' 3' di phenyl spiro acenaphthen 1 one 2 4' azetidin 2' ones novel examples exhibiting a high reactivity of imino group in ketimines



Canadian Journal of Chemistry 60(14): 1901-1906



The reaction of 2-diazo-1,2-diphenylethanone (1) with 2-imino-1,2-diphenylethanones 2a-e gave new N-substituted 3,3,4-triphenyl-4-benzoylazetidin-2-ones 3a-e, together with 1,1',2,2'-tetraphenyl-2,2'-azinodiethanone (4). Similar reaction of 1 with 2-iminoacenaphthenones 6a, b yielded N-substituted 3',3'-diphenyl spiro(acenaphthen-1-one-2,4'-azetidin-2'-ones) 7a, b and ketazine 4. Lithium aluminium hydride reduction of azetidinones 3a, b gave 4-.alpha.-hydroxybenzylazetidin-2-ones 5a, b. The spiro azetidinones 7a, b on reduction with sodium borohydride yielded spiro(1-hydroxyacenaphthene-2,4'-azetidin-2-ones) 8a, b. The azetidinones 3a-e and 7a, b were unaffected by acid or base hydrolysis. The marked selective reactivity of the imino group as compared to the carbonyl group towards diphenylketene was observed in the present studies. The comparative reactivity of carbonyl groups present in azetidinones 3a, b and 7a, b was presented. [This study relates to the synthesis of .beta.-lactam antibiotics.].

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