31562-05-7Relevant academic research and scientific papers
Synthesis, Stability, Structure, Reactivity, and Chemistry of N-Alkylbenzoazetinones
Olofson, R. A.,Vander Meer, Robert K.,Hoskin, Dennis H.,Bernheim, Marguerite,Stournas, Stamoulis,Morrison, David S.
, p. 3367 - 3372 (2007/10/02)
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'-adamantylbenzoazetino
Reactions of Anthranilium Salts with Nucleophiles: Adduct Formation and Rearrangement
Vander Meer, Robert K.,Olofson, R. A.
, p. 3373 - 3377 (2007/10/02)
3-Unsubstituted anthranilium salts 1 react with alcohols in the presence of bases to yield adducts 5 which rearrange to the esters 4 when refluxed in xylene.Similar processes involving 1 and cyanide or azide also have been observed.Evidence favoring benzoazetinones 2 as rearrangement intermediates is presented.The chemistry of 1 with phosphines and phosphites is also described.For example, treatment of 1c with trimethyl phosphite yields the rearranged adduct salt 14 which cleaves to the acyl phosphonate 15 when treated with triethylamine.
