Title
On the importance of an acid additive in the synthesis of pyrido[1,2-a]benzimidazoles by direct copper-catalyzed aminationOn the importance of an acid additive in the synthesis of pyrido[1,2-a]benzimidazoles by direct copper-catalyzed amination
Author
Faculty/Department
Faculty of Sciences. Chemistry
Research group
Organic synthesis
Molecular Spectroscopy
Publication type
article
Publication
Weinheim,
Subject
Chemistry
Source (journal)
Chemistry: a European journal. - Weinheim
Volume/pages
17(2011):23, p. 6315-6320
ISSN
0947-6539
ISI
000292095800005
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
Not just an acid! An expedient and highly modular synthesis of 6-, 7-, and 8-substituted pyrido[1,2-a]benzimidazoles (4) has been developed by a direct intramolecular C[BOND]H amination of N-phenylpyridin-2-amines (3). Efficient C[BOND]H amination of 3 could only be achieved in the presence of catalytic copper and an acid additive. The type of acid (pKa) proved to be crucial for the catalysis. C[BOND]Cl aminations in N-(2-chloroaryl)pyridin-2-amines allow access to 9-substituted pyrido[1,2-a]benzimidazoles.
E-info
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