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Direct intramolecular double cross-dehydrogentive-coupling (CDC) cyclization of N-(2-pyridyl)amidines under metal-free conditions.

ABSTRACT: A facile transition-metal-free protocol to form 2-iminoimidazo[1, 2-a]-pyridines bearing a -CHBr₂ group and an aza-quaternary carbon center at the 3 position from N-(2-pyridyl)amidines substrates, in which the new heterocyclic skeletons constructed from amidines via radical reactions or nucleophilic substitution reactions are promoted only by CBr₄ under mild conditions, is demonstrated. The reactions were realized by intramolecular CDC reaction involving C-N and C-C bond formation via the sequential C(sp³)-H bifunctionalization mode on the same carbon atom under mild conditions. Moreover, this work also provides an excellent and representative example for CBr₄ as an efficient reagent to initiate radical reactions under initiator-free conditions or to give rise to nucleophilic substitution reactions only by base.

SUBMITTER: Yi F

PROVIDER: S-EPMC9076575 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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Direct intramolecular double cross-dehydrogentive-coupling (CDC) cyclization of N-(2-pyridyl)amidines under metal-free conditions.

Yi Fengping F Fu Chao C Sun Qihui Q Wei Huazhen H Yu Genfa G Yi Weiyin W

RSC advances 20191219 72

A facile transition-metal-free protocol to form 2-iminoimidazo[1, 2-a]-pyridines bearing a -CHBr2 group and an aza-quaternary carbon center at the 3 position from N-(2-pyridyl)amidines substrates, in which the new heterocyclic skeletons constructed from amidines via radical reactions or nucleophilic substitution reactions are promoted only by CBr4 under mild conditions, is demonstrated. The reactions were realized by intramolecular CDC reaction involvin ...[more]

PMID: 35542831

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