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Synlett 2019; 30(05): 625-629
DOI: 10.1055/s-0037-1612082
letter
© Georg Thieme Verlag Stuttgart · New York

Iodine-Mediated Multicomponent Synthesis of 3-Sulfenylimidazo[1,2-a]pyridines from 2-Aminopyridines, Ketones, and Sulfonyl Hydrazides

Sipei Hu
,
Shiying Du
,
Yunjie Yao
,
Zuguang Yang
,
Hongjun Ren*
,
Zhengkai Chen  *
Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. of China   Email: renhj@zstu.edu.cn   Email: zkchen@zstu.edu.cn
› Author AffiliationsWe thank the financial support from the National Natural Science Foundation of China (Grant No. 21602202) and the Natural Science Foundation of Zhejiang Province (Grant No. LY19B020016).
Further Information

Publication History

Received: 05 November 2018

Accepted after revision: 26 December 2018

Publication Date:
13 February 2019 (online)

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Abstract

A one-pot multicomponent reaction for the synthesis of 3-sulfenylimidazo[1,2-a]pyridines from readily available 2-aminopyridines, ketones, and sulfonyl hydrazides, mediated by molecular iodine, has been developed. The transformations proceed smoothly with high efficiency and a broad substrate scope, affording the desired heterocyclic products in moderate to excellent yields.

Key words

metal-free synthesis - multicomponent reaction - C–S bond formation - imidazopyridines - N-heterocyclic compounds

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1612082.
  • Supporting Information
 

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  • 15 2-Phenyl-3-(4-tolylthio)imidazo[1,2-a]pyridine (4a); Typical Procedure PPh3 (157.4 mg, 0.6 mmol) and I2 (38.1 mg, 0.15 mmol) were added to a solution of amine 1a (0.3 mmol), ketone 2a (0.42 mmol), and sulfonyl hydrazide 3a (0.6 mmol) in DMSO (1 mL), and the mixture was stirred at 100 °C under air for 12 h. When the reaction was complete (TLC), the mixture was cooled to r.t. The reaction was quenched with H2O, and the mixture was extracted with EtOAc (3 × 15 mL). The extracts were washed with 10% aq Na2S2O3 (2 × 15 mL), dried (Na2SO4), and concentrated in vacuo to provide a crude product, that was purified by column chromatography (silica gel, PE–EtOAc) to give a white solid; yield: 77 mg (81%); mp 136–138 °C. 1H NMR (400 MHz, CDCl3): δ = 8.28 (d, J = 6.8 Hz, 1 H), 8.22 (d, J = 7.6 Hz, 2 H), 7.72 (d J = 9.2 Hz, 1 H,), 7.44 (t, J = 7.4 Hz, 2 H), 7.38 (d, J = 7.2 Hz, 1 H), 7.32 (t, J = 8 Hz, 1 H), 7.02 (d, J = 8 Hz, 2 H), 6.91 (d, J = 8 Hz, 2 H), 6.86 (t, J = 6.8 Hz, 1 H), 2.26 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 151.2, 147.0, 136.0, 133.4, 131.5, 130.2, 128.5, 128.4, 126.5, 125.9, 124.5, 117.6, 113.0, 106.9, 20.9. HRMS (ES+-TOF): m/z [M + H]+ calcd for C20H17N2S: 317.1107; found: 317.1116.
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