On the Importance of an Acid Additive in the Synthesis of Pyrido[1,2‐ a ]benzimidazoles by Direct Copper‐Catalyzed Amination | Zendy

Masters KyeSimeon | Zendy; Rauws Tom R. M. | Zendy; Yadav Ashok K. | Zendy; Herrebout Wouter A. | Zendy; Van der Veken Benjamin | Zendy; Maes Bert U. W. | Zendy

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On the Importance of an Acid Additive in the Synthesis of Pyrido[1,2‐ a ]benzimidazoles by Direct Copper‐Catalyzed Amination

Author(s) -

Masters KyeSimeon,

Rauws Tom R. M.,

Yadav Ashok K.,

Herrebout Wouter A.,

Van der Veken Benjamin,

Maes Bert U. W.

Publication year - 2011

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201100574

Subject(s) - amination , intramolecular force , catalysis , chemistry , copper , combinatorial chemistry , modular design , organic chemistry , computer science , operating system

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 CH amination of N ‐phenylpyridin‐2‐amines ( 3 ). Efficient CH amination of 3 could only be achieved in the presence of catalytic copper and an acid additive. The type of acid (p K a ) proved to be crucial for the catalysis. CCl aminations in N ‐(2‐chloroaryl)pyridin‐2‐amines allow access to 9‐substituted pyrido[1,2‐ a ]benzimidazoles.

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