
%0 Journal Article
%A Candeloro, V 
%A Bowie, JH 
%T 1H-1-Benzazepines. The reactions of laevulinic acid and &#946;-benzoylpropionic acid with aniline and methoxyanilines
%J Australian Journal of Chemistry
%D 1978/09/01
%V 31
%N 9
%P 2031-2037
%K 
%R https://doi.org/10.1071/CH9782031
%U https://www.publish.csiro.au/paper/CH9782031 
%X Treatment of laevulinic acid with aniline yields 5-methyl-2,3-dihydro- 1H-1-benzazepin-2-one and 5-(2-methyl-5-oxo-1-phenylpyrrolidin-2-yl)-4- oxo-N-phenylpentanamide In contrast, the reaction between &#946;- benzoylpropionic acid and aniline yields 4-(2-oxo-1,5-diphenyl-2,3- dihydropyrrol-3-ylidene)-N,4-diphenylbutanamide, whose structure is confirmed by an independent synthesis. The yield of the latter type of reaction is enhanced if p-methoxyaniline is used, whereas the desired benzazepine is obtained if m-methoxyaniline is utilized. For example, the reaction between &#946;-benzoyl-propionic acid and m-methoxyaniline yields 8-methoxy-5-phenyl-2,3-dihydro-1H-1-benzazepine-2-one as the major cyclized product. 
