Sequential Groebke–Blackburn–Bienaymé and Pictet–Spengler Reactions for Regioselective Synthesis of Polyheterocyclics

Organic Letters 2026

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Authors: Wan Sin Lim, Ashutosh Nath, Takeru Saito, Wei Zhang
DOI: 10.1021/acs.orglett.6c00878
Cited by: 3
References: 19

Abstract

A two-step process involving Groebke-Blackburn-Bienaymé (GBB) and Pictet-Spengler (PS) reactions is developed for the regioselective synthesis of a unique polycyclic scaffold containing benzazepine, imidazopyridine, and dihydropyrroloazepine rings. Density functional theory calculations indicate that the C4 position on indole is kinetically favorable for the PS reaction to give benzazepine compounds as single products.

Fields of Study & Subjects

Synthesis and pharmacology of benzodiazepine derivatives Synthesis of heterocyclic compounds Multicomponent Synthesis of Heterocycles

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
15
Pages
4811–4815
Publication date
8 April 2026
Language
EN