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Cu(I)-Catalyzed Aminative Aza-Annulation of Enynyl Azide using N-Fluorobenzenesulfonimide: Synthesis of 5-Aminonicotinates

Author:
Reddy, Chada Raji, Prajapti, Santosh Kumar, Ranjan, Ravi
Source:
Organic letters 2018 v.20 no.10 pp. 3128-3131
ISSN:
1523-7052
Subject:
amination, azides, chemical bonding, chemical structure, copper, nitrogen, regioselectivity
Abstract:
An unprecedented copper-catalyzed aminative aza-annulation of enynyl azide using commercially available N-fluorobenzenesulfonimide (NFSI) as an amination reagent is described. The reaction proceeds via regioselective inter-/intramolecular diamination, incorporating one nitrogen from the NFSI and the other from the azide, to provide amino-substituted nicotinate derivatives in a single step with moderate to high yield. This method represents an efficient way to access diverse aminonicotinates through direct C–N bond-coupling processes.
Agid:
6084035