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

Wan Sin Lim; Ashutosh Nath; Takeru Saito; Wei Zhang

doi:10.1021/acs.orglett.6c00878

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

Wan Sin Lim
, Ashutosh Nath
, Takeru Saito
, Wei Zhang

Chemistry

University of Massachusetts Boston

Research output: Contribution to journal › Letter › peer-review

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.

Original language	English
Pages (from-to)	4811-4815
Number of pages	5
Journal	Organic Letters
Volume	28
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.6c00878
State	Published - Apr 17 2026

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Sequential Groebke{\textendash}Blackburn{\textendash}Bienaym{\'e} and Pictet{\textendash}Spengler Reactions for Regioselective Synthesis of Polyheterocyclics",

abstract = "A two-step process involving Groebke{\textendash}Blackburn{\textendash}Bienaym{\'e} (GBB) and Pictet{\textendash}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.",

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AU - Lim, Wan Sin

AU - Nath, Ashutosh

AU - Saito, Takeru

AU - Zhang, Wei

PY - 2026/4/17

Y1 - 2026/4/17

N2 - 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.

AB - 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.

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UR - https://www.scopus.com/pages/publications/105035916288#tab=citedBy

U2 - 10.1021/acs.orglett.6c00878

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SP - 4811

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JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

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

Abstract

ASJC Scopus Subject Areas

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