Abstract
An efficient synthesis of hexahydropyrrolo[3,2-c]quinolin-2-ones and hexahydropyridino[3,2-c]quinolin-2-ones has been developed in moderate to high yields by one-pot two-step aza-Diels–Alder reactions of N-arylimines, formed in situ from anilines and benzaldehydes, with cyclic enamides, formed in situ from 5-hydroxypyrrolidin-2-ones and 6-hydroxypiperidin-2-ones by BF3·OEt2-promoted dehydration in dichloromethane at room temperature. The hexahydropyrrolo[3,2-c]quinolin-2-ones were formed as a single exo-stereoisomer in most cases and hexahydropyridino[3,2-c]quinolin-2-ones were formed as a mixture of exo- and endo-isomers favoring the endo-diastereomer.
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