Novel synthesis of the 2-benzazepine system

Gold(I)-Catalyzed Benz[c]azepin-4-ol Synthesis by Intermolecular [5 + 2] Cycloaddition

“…To study whether the significantly less reactive propargyl esters would undergo gold(I)-catalyzed [2 + 5] cycloaddition in a similar way, reactions of propargyl ester 1g with imines 2a,b were performed. The reactions afforded considerably lower yields of the corresponding benzazepine esters 5a,b (34−47%, entry 19), and full conversion could not be obtained, even within several days of reflux.…”

“…Benz­[ c ]­azepin-4-one derivatives have been prepared by ester condensation and ring closure with formaldehyde . Alternatively, intramolecular acylation has afforded functionalized benz­[ c ]­azepin-4-ones by cyclization through C4–C5 bond formation . Benz­[ c ]­azepin-3-ones, potentially good candidates for new drug therapies to treat skin wounds, were prepared via an intramolecular Friedel–Crafts reaction .…”

“…17e Alternatively, intramolecular acylation has afforded functionalized benz [c]azepin-4-ones by cyclization through C4−C5 bond formation. 19 Benz [c]azepin-3-ones, potentially good candidates for new drug therapies to treat skin wounds, were prepared via an intramolecular Friedel−Crafts reaction. 1 Compounds based on the general 4-oxo structure E (2,3-dihydro-1H-benz [c]azepin-4(5H)-one) or the corresponding enol form E′ have been studied due to their structural similarities with bioactive natural alkaloids and, thus, potential biological activity.…”