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A Direct Cycloaminative Approach to Imidazole Derivatives via Dual C–H Functionalization

Author:
Arepally, Sagar, Babu, Venkata Nagarjuna, Bakthadoss, Manickam, Sharada, Duddu S.
Source:
Organic letters 2017 v.19 no.19 pp. 5014-5017
ISSN:
1523-7052
Subject:
carbenes, carbon-hydrogen bond activation, chemical bonding, chemical reactions, chemical structure, imidazoles
Abstract:
Organoiodine(III)-promoted C(sp³)–H azidation was a key step for the cycloaminative process. An unprecedented method for metal-free dehydrogenative N-incorporation into C(sp³)–H and C(sp²)–H bonds for the synthesis of diverse imidazoles has been disclosed. The overall transformation involves the construction of four C–N bonds through hydroamination-azidation-cyclization sequence. The reaction can be easily handled and proceeds under mild conditions. Further, the potential of the present strategy is revealed by the practical synthesis of N-heterocyclic carbene (NHC) precursors.
Agid:
5826915