2-Benzazepine Analogues from d-Glucose: Synthesis of Chiral cis- and trans-Fused Furo[3,2-c][2]benzazepine Derivatives

Abstract

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.

Key words

furans - azepines - cyclizations - palladium - carbohydrates

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15

¹H NMR assignments are based on ¹H-¹H COSY results.

18

Restricted rotation of the amide CN bonds in the carbamate derivatives of benzazepines (12a-c, 14, 15 or 16) are likely to have caused multiplicity of ¹H and ¹³C signals (in 1:1 or 1:2 ratio).