Double Ring Expansion Strategy for Fused 3‑Benzazepines: Alternative Synthesis of the Dolby–Weinreb Enamine

• Published in: Journal of organic chemistry Vol. 87; no. 24; pp. 16947 - 16951
• Main Authors: Saito, Keigo, Aoyama, Hiroshi, Sako, Makoto, Arisawa, Mitsuhiro, Murai, Kenichi
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 16.12.2022; Amer Chemical Soc
• Subjects: Alkaloids; Benzazepines; Chemistry; Chemistry, Organic; Molecular Structure; Physical Sciences; Science & Technology; REARRANGEMENT; AMINES; CEPHALOTAXINE

A double ring expansion strategy for constructing fused 3-benzazepines is described. The oxidative ring expansion of spiroamine compounds with N-chlorosuccinimide and subsequent ring expansion of the resulting ketiminium ion intermediates with trimethylsilyldiazomethane afforded fused 3-benzazepines...