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

Yanpeng Liu; Lixue Lu; Haipin Zhou; Feijie Xu; Cong Ma; Zhangjian Huang; Jinyi Xu; Shengtao Xu

doi:10.1039/c9ra06724h

Author(s)

Lixue Lu
Haipin Zhou
Feijie Xu
Cong Ma
Zhangjian Huang
Jinyi Xu
Shengtao Xu

Related Research Unit(s)

Department of Chemistry

Detail(s)

Original language	English
Pages (from-to)	34671-34676
Journal / Publication	RSC Advances
Volume	9
Issue number	59
Online published	28 Oct 2019
Publication status	Published - 2019

Link(s)

DOI	DOI https://doi.org/10.1039/c9ra06724h Final Published version
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Attachment(s)	Documents 39614138.pdf Final Published version, 892 KB, PDF Publisher's Copyright Statement This full text is made available under CC-BY-NC 3.0. https://creativecommons.org/licenses/by-nc/3.0/
Link to Scopus	https://www.scopus.com/record/display.uri?eid=2-s2.0-85074544105&origin=recordpage
Permanent Link	https://scholars.cityu.edu.hk/en/publications/publication(9674db32-3103-4683-b6f8-7260a4e3f269).html

Abstract

N-(Pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines were synthesized respectively from alpha-bromoketones and 2-aminopyridine under different reaction conditions. N-(Pyridin-2-yl)amides were formed in toluene via C-C bond cleavage promoted by I-2 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.

Research Area(s)

AEROBIC OXIDATIVE SYNTHESIS, AMIDE BOND FORMATION, CARBOXYLIC-ACIDS, COPPER, INHIBITORS, CLEAVAGE, KETONES, DESIGN, ESTERS, AMIDATION

Citation Format(s)

[ RIS ] [ BibTeX ]

Chemodivergent synthesis of N-(pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines from α-bromoketones and 2-aminopyridines. / Liu, Yanpeng; Lu, Lixue; Zhou, Haipin; Xu, Feijie; Ma, Cong; Huang, Zhangjian; Xu, Jinyi; Xu, Shengtao.

In: RSC Advances, Vol. 9, No. 59, 2019, p. 34671-34676.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62) › 21_Publication in refereed journal › peer-review

Liu, Y, Lu, L, Zhou, H, Xu, F, Ma, C, Huang, Z, Xu, J & Xu, S 2019, 'Chemodivergent synthesis of N-(pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines from α-bromoketones and 2-aminopyridines', RSC Advances, vol. 9, no. 59, pp. 34671-34676. https://doi.org/10.1039/c9ra06724h

Liu, Y., Lu, L., Zhou, H., Xu, F., Ma, C., Huang, Z., Xu, J., & Xu, S. (2019). Chemodivergent synthesis of N-(pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines from α-bromoketones and 2-aminopyridines. RSC Advances, 9(59), 34671-34676. https://doi.org/10.1039/c9ra06724h

Liu Y, Lu L, Zhou H, Xu F, Ma C, Huang Z et al. Chemodivergent synthesis of N-(pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines from α-bromoketones and 2-aminopyridines. RSC Advances. 2019;9(59):34671-34676. https://doi.org/10.1039/c9ra06724h

Liu, Yanpeng ; Lu, Lixue ; Zhou, Haipin ; Xu, Feijie ; Ma, Cong ; Huang, Zhangjian ; Xu, Jinyi ; Xu, Shengtao. / Chemodivergent synthesis of N-(pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines from α-bromoketones and 2-aminopyridines. In: RSC Advances. 2019 ; Vol. 9, No. 59. pp. 34671-34676.

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