Synlett 2017; 28(18): 2499-2504
DOI: 10.1055/s-0036-1589083
letter
© Georg Thieme Verlag Stuttgart · New York

Ammonium Iodide-Mediated Sulfenylation of 4-Hydroxycoumarins or 4-Hydroxyquinolinones with a Sulfonyl Chloride as a Sulfur Source

Tao Guo*a, b, Xu-Ning Weia
  • aSchool of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou, Henan 450001, P. R. of China   Email: taoguo@haut.edu.cn
  • bSchool of Pharmaceutical Sciences, Zhengzhou University, 100 Kexue Avenue, Zhengzhou, Henan 450001, P. R. of China
Financial support from Open Project of Grain and Corn Engineering Technology Research Center in State Administration of Grain (No. 24400042), the Doctoral Fund of Henan University of Technology (No. 2013BS053), the Colleges and Universities Key Research Program Foundation of Henan Province (No. 17A150006), the Science and Technology Foundation of Henan Province (No. 172102310621), and the Fundamental Research Funds for the Henan Provincial Colleges and Universities in Henan University of Technology (No. 2015QNJH08) are greatly appreciated
Further Information

Publication History

Received: 31 May 2017

Accepted after revision: 03 July 2017

Publication Date:
02 August 2017 (eFirst)

Abstract

A novel ammonium iodide-induced sulfenylation of 4-hydroxycoumarins or 4-hydroxyquinolinones by using an aryl- or alkylsulfonyl chloride as the sulfur source gave a wide range of 3-sulfanyl-4-hydroxycoumarins or 3-sulfanyl-4-hydroxyquinolinones, respectively, in moderate to good yields. This method provides as a simple approach to the direct formation of C–S bonds, which is of high value and utility in the pharmaceutical industry.

Supporting Information

 
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  • 14 4-Hydroxy-3-sulfanylquinolin-2(1H)-ones 3ao and 4-Hydroxy-3-sulfanyl-2H-chromen-2-ones 5aq; General Procedure 1,4-Dioxane (0.5 mL) was added to flask charged with the appropriate 4-hydroxyquinolinone or 4-hydroxycoumarin (0.25 mmol), sulfonyl chloride (0.25 mmol), and NH4I (1 mmol), and the mixture was stirred at 110 °C under air for 6–12 hours until the reaction was complete (TLC). The mixture was then cooled to r.t., diluted with EtOAc (20 mL), and washed with H2O (10 mL). The aqueous layer was extracted with EtOAc (2 × 5 mL), and the organic phases were combined and dried (Na2SO4). After evaporation of the solvents, the residue was purified by flash column chromatography [silica gel, PE–EtOAc (4:1 to 1:1)] to afford the desired product 3 or 5. 4-Hydroxy-1-methyl-3-(4-tolylsulfanyl)quinolin-2(1H)-one (3a)[11]
    Yellow solid; yield: 58 mg (78%); mp 234–236 °C. IR (KBr): 2922, 2362, 1614, 1583, 1500, 1159, 1074, 802, 756 cm–1. 1H NMR (400 MHz, CDCl3): δ = 2.26 (s, 3 H), 3.71 (s, 3 H), 7.03 (d, J = 8.0 Hz, 2 H), 7.22–7.30 (m, 3 H), 7.36 (d, J = 8.8 Hz, 1 H), 7.65 (td, J = 1.6, 8.8 Hz, 1 H), 7.90 (s, 1 H), 8.06 (dd, J = 1.2, 8.0 Hz, 1 H). 13C NMR (125 MHz, CDCl3): δ = 21.1, 30.3, 103.2, 114.3, 114.4, 122.1, 125.1, 128.7, 130.1, 130.7, 132.8, 137.0, 140.4, 161.8, 163.2. HRMS: m/z [M + H]+ calcd for C17H16NO2S: 298.0896; found: 298.0909. 4-Hydroxy-3-(phenylsulfanyl)-2H-chromen-2-one (5a)[11] Yellow solid; yield: 54 mg (80 %); mp 198–200 °C. 1H NMR (400 MHz, DMSO-d 6): δ = 7.15–7.21 (m, 3 H), 7.29 (d, J = 8.0 Hz, 2 H), 7.40–7.45 (m, 2 H), 7.70–7.75 (m, 1 H), 7.97 (dd, J = 1.2, 8.0 Hz, 1 H). 13C NMR (100 MHz, DMSO-d 6): δ = 94.3, 115.7, 116.5, 124.2, 124.4, 125.5, 126.2, 129.1, 133.7, 135.9, 153.0, 160.9, 168.5. HRMS: m/z [M + H]+ calcd for C15H11O3S: 271.04234; found: 271.04205.