Synthesis, stability, structure, reactivity, and chemistry of N-alkylbenzoazetinones

RA Olofson, RK Vander Meer, DH Hoskin…

Index: Olofson, R. A.; Vander Meer, Robert K.; Hoskin, Dennis H.; Bernheim, Marguerite; Stournas, Stamoulis; Morrison, David S. Journal of Organic Chemistry, 1984 , vol. 49, # 18 p. 3367 - 3372

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Citation Number: 29

Abstract

On treatment with triethylamine, 3-unsubstituted anthranilium salts 1 ring open and then recyclize to N-alkylbenzoazetinones 3. When the alkyl group is tertiary, 3 is stable and the X- ray crystal structure of one such derivative, N-1'-adamantylbenzoazetinone (3g), requires a planar antiaromatic formulation with some bond localization in the benzo moiety. Ring- cleavage products are obtained in the rapid reaction of the@-lactams 3 with nucleophiles ...