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Chemodivergent synthesis of N-(pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines from α-bromoketones and 2-aminopyridines.

ABSTRACT: N-(Pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines were synthesized respectively from α-bromoketones and 2-aminopyridine under different reaction conditions. N-(Pyridin-2-yl)amides were formed in toluene via C-C bond cleavage promoted by I2 and TBHP and the reaction conditions were mild and metal-free. Whereas 3-bromoimidazopyridines were obtained in ethyl acetate via one-pot tandem cyclization/bromination when only TBHP was added, the cyclization to form imidazopyridines was promoted by the further bromination, no base was needed, and the versatile 3-bromoimidazopyridines could be further transferred to other skeletons.

SUBMITTER: Liu Y 

PROVIDER: S-EPMC9073897 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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Chemodivergent synthesis of <i>N</i>-(pyridin-2-yl)amides and 3-bromoimidazo[1,2-<i>a</i>]pyridines from α-bromoketones and 2-aminopyridines.

Liu Yanpeng Y   Lu Lixue L   Zhou Haipin H   Xu Feijie F   Ma Cong C   Huang Zhangjian Z   Xu Jinyi J   Xu Shengtao S  

RSC advances 20191028 59

<i>N</i>-(Pyridin-2-yl)amides and 3-bromoimidazo[1,2-<i>a</i>]pyridines were synthesized respectively from α-bromoketones and 2-aminopyridine under different reaction conditions. <i>N</i>-(Pyridin-2-yl)amides were formed in toluene <i>via</i> C-C bond cleavage promoted by I<sub>2</sub> and TBHP and the reaction conditions were mild and metal-free. Whereas 3-bromoimidazopyridines were obtained in ethyl acetate <i>via</i> one-pot tandem cyclization/bromination when only TBHP was added, the cycliza  ...[more]

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