Treatment of laevulinic acid with aniline yields 5-methyl-2,3-dihydro-lH-l-benzazepin-2-0ne and 5-(2-methyl-5-oxo-l-phenylpyrrolidin-2-yl)-4-oxo-N-phenylpentanamide In contrast, the reaction between P-benzoylpropionic acid and aniline yields 4-(2-0~0-1,5-dipheny1-2,3-dihydropyrrol-3-y1idene)-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 P-benzoylpropionic acid and m-methoxyaniline yields 8-methoxy-5-phenyl-2,3-dihydro-lH-l-benzazepine-2-one as the major cyclized product.
Treatment of 8-substituted (H, Me, MeO) 5-methyI-l,3-dihydro-ZH-l -benzazepin-2-ones with phosphoryl chloride under reflux produces two products. X-Ray structure determination of the products from the 8-methoxy derivative shows them to be 2,12-dimethoxy-5,9-dimethyl-7H-[l] benzazepino-[1',2': 1,2]pyrrol0[5,4-b]quinoline (major product) and 5-chloromethyl-2,ll -dimethoxy-5,8-dimethyl -5,6-d i hydroqu i no [ 1 ', 2' : 1 ,2] pyrrolo-[ 5,4-61 q u i no1 i ne (mi nor product) . The corresponding reaction of 8-met hoxy-5-phenyl -1,3-di hydro-2H-1benzaze pi n-2-one yields 2,12-dimethoxy-5,9diphenyl-7H-[l]benzazepino[1',2': 1,2]pyrrol0[5,4-6]quinoline as the sole product.A mechanistic pathway is proposed in which the first step involves condensation of two molecules of the appropriate 2-chloro-5-methyl-1 H-1 -bemazepine or its 3H analogue.
Für die Bildung der Verbindungen (V) und (VI) wird eine mechanistische Erklärung gegeben, derzufolge die Dihydrobenzazepinone (III) von POCl3 zuerst zu den Benzazepinen (IV) chloriert werden, die sich unter Umlagerung und HCl‐Eliminierung dimerisieren.
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