Premium
Homologation of the Fischer Indolization: A Quinoline Synthesis via Homo‐Diaza‐Cope Rearrangement
Author(s) -
Gerosa Gabriela Guillermina,
Schwengers Sebastian Armin,
Maji Rajat,
De Chandra Kanta,
List Benjamin
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202005798
Subject(s) - quinoline , brønsted–lowry acid–base theory , indole test , chemistry , pyridine , cope rearrangement , catalysis , aryl , combinatorial chemistry , stereochemistry , organic chemistry , alkyl
We disclose a new Brønsted acid promoted quinoline synthesis, proceeding via homo‐diaza‐Cope rearrangement of N ‐aryl‐ N ′‐cyclopropyl hydrazines. Our strategy can be considered a homologation of Fischer's classical indole synthesis and delivers 6‐membered N‐heterocycles, including previously inaccessible pyridine derivatives. This approach can also be used as a pyridannulation methodology toward constructing polycyclic polyheteroaromatics. A computational analysis has been employed to probe plausible activation modes and to interrogate the role of the catalyst.