The Diels‐Alder reactions of 3,4‐dihydro‐5H‐1‐benzazepine‐2,6,9‐trione 1 with butadiene, cyclopentadiene, 1‐(E)‐trimethylsiloxybutadiene 4, and methacrolein dimethylhydrazone are described. Cycloaddition with the unsymmetrical dienes 4 and 18 occurs regiospecifically affording 5 and 19 respectively. The structure of 5 was established through naphthazepine 13 by comparison of its 1H nmr with model compounds. The probable course of cycloaddition with 1‐azadiene 18 is analyzed considering the polarization of azadiene 18 and the behavior of quinone 1 in the reaction with 4. Michael addition of quinone 1 with isobutenylmorpholine 23 which afforded exclusively the cyclic O,N‐acetal 24 or 25 and its convertion to benzepinquinone 26 or 27 is also reported.
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Valderrama et al. (1992) studied this question.
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