Issue 72, 2019, Issue in Progress

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
08 Nov 2019
Accepted
06 Dec 2019
First published
19 Dec 2019
This article is Open Access
Creative Commons BY license

RSC Adv., 2019,9, 42172-42182

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

F. Yi, C. Fu, Q. Sun, H. Wei, G. Yu and W. Yi, RSC Adv., 2019, 9, 42172 DOI: 10.1039/C9RA09265J

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