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CuI/I 2 ‐Mediated Intramolecular Oxidative Cyclization Reaction of N ‐(2‐pyridyl)amidines by the Direct Double C−H Functionalization of a C(sp 3 )−H Bond
Author(s) -
Yi Fengping,
Zhang Songxing,
Zhang Lirong,
Yi Weiyin,
Yu Rui
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700442
Subject(s) - chemistry , intramolecular force , reactivity (psychology) , substrate (aquarium) , medicinal chemistry , catalysis , sulfonyl , reaction conditions , stereochemistry , organic chemistry , medicine , oceanography , alternative medicine , alkyl , pathology , geology
A facile approach to a rare class of 3,3‐disubstituted 2‐iminoimidazo[1,2‐ a ]‐pyridines bearing a hydroxyl group at the 3 position in good to excellent yields from N ‐(2‐pyridyl)amidines substrates in the presence of CuI/I 2 /KI/KO t Bu is described. According to the investigation, the use of a Cu catalyst and the presence of sulfonyl groups in the substrates has a remarkable influence on the success of the oxidative cyclization reaction. Moreover, the oxygen source of the hydroxyl group may be from the incorporation of water in the reaction system or KO t Bu. The successful implementation of the reaction further indicates that amidines have abundant reactivity under various reaction conditions. The methodology is operationally simple and has a broad substrate scope.