2-Benzazepine analogues from D-glucose: Synthesis of chiral cis- and trans-fused furo[3,2-c][2]benzazepine derivatives

摘要

Facile annulation of benzazepines onto furano-sugars has been achieved through Pd-catalyzed intramolecular cyclization. Using diisopropylidene D-glucose as a starting material, the first chiron approach to furobenzazepines in both cis and trans forms selectively introduced a 7-membered azepine ring linearly fused to a sugar nucleus. Cleavage of the sugar ring of the tricyclic derivatives provide a convenient route for entry into chiral functionalized 2-benzazepines, viz. 15 from 12a, and 16 from 14.