3-芳硫基-4-羟基香豆素及其类似物的制备

doi:10.11944/j.issn.1000-0518.2018.10.170406

摘要/Abstract

摘要：

4-羟基香豆素类化合物与4-羟基喹啉酮类化合物是一类重要的有机杂环化合物,因为其良好的生理活性,被广泛应用于抗菌、抗炎、抗HIV、抗肿瘤等药物结构中。本文用4-羟基香豆素类化合物或4-羟基喹啉酮类化合物作为底物、以硫磺粉(S)为硫源、以碘苯类衍生物作为芳基源,在氯化铜催化作用下合成了3-芳硫基-4-羟基香豆素类化合物和3-芳硫基-4-羟基喹啉酮类化合物。该方法使用环境友好的硫磺粉为硫源替代有机硫,操作简单、无污染、成本低廉,为该类化合物的绿色合成提供了新的方案。

关键词: 芳硫基-羟基香豆素, 芳硫基-羟基喹啉酮, 芳硫基化

Abstract:

4-Hydroxylcoumarin and its analogs are one of the most active classes of heterocyclic compounds. Many of these compounds have been proved to have a wide range of biological and pharmacological activities, such as antibacterial, anti-tumor, anti-HIV. Herein, 3-arylthio-4-hydroxycoumarin and its analogs were synthesized from stable non-toxic 4-hydroxycoumarins, iodobenzenes and sulfur in a cheap and environmentally friendly fashion.

Key words: arylthio-hydroxycoumarin, arylthio-hydroxyquinolinone, aryl-thiolation

王宏雁, 委旭宁. 3-芳硫基-4-羟基香豆素及其类似物的制备[J]. 应用化学, 2018, 35(10): 1184-1189.

WANG Hongyan, WEI Xuning. Preparation of 3-Arylthio-4-hydroxycoumarin and Its Analogs[J]. Chinese Journal of Applied Chemistry, 2018, 35(10): 1184-1189.

参考文献

[1]	LI Jing.Studies on Microwave Synthesis,Spectroscopic and Electrochemical Properties of 4-Hydroxycoumarin and Its Derivatives[D]. Xi'an:Xi'an University of Architecture and Technology,2008(in Chinese). 李靖. 4-羟基香豆素及其衍生物的微波合成,光谱及电化学性质研究[D]. 西安:西安建筑科技大学,2008.
[2]	ZHI Shuang,WEN Weidong,YANG Guifang,et al. Study on the Fluorescence Spectra and Application Properties of Coumarin Dyes[J]. Dyes Color,2005,42(4):24-26(in Chinese). 智双,温卫东,杨桂芳,等. 香豆素类染料的荧光光谱性能及应用性能研究[J]. 染料与染色,2005,42(4):24-26.
[3]	ZHANG Zhiping.New Development of Quinolone Antibacterials[J]. Chinese J Antibiot,1999,24(1):61-68(in Chinese). 张致平. 喹诺酮类抗菌药研究的新进展[J]. 中国抗生素杂志,1999,24(1):61-68.
[4]	Equbal D,Lavekar A,Sinha A.Cooperative Catalysis by Bovine Serum Albumin-iodine Towards Cascade Oxidative Coupling-C(sp 2)-H Sulfenylation of Indoles/Hydroxyaryls with Thiophenols on Water[J]. Org Biomol Chem,2016,14(25):6111-6118.
[5]	Rajesha G,Mahadevan K,Satyanarayan N,et al. Synthesis, Antibacterial, and Analgesic Activity of Novel 4-Hydroxy-3-(Phenylthio)-2-H-Chromen-2-Ones and 4-Hydroxy-3-[Imidazol/Tetrazolo-2-yl)thio]-2-H-Chromen-2-Ones[J]. Phosphorus Sulfur,2011,186(8):1733-1743.
[6]	Paul S,Shrestha R,Edison T,et al. Copper(Ⅰ) Bromide Dimethyl Sulfide Catalyzed Direct Sulfanylation of 4-Hydroxycoumarins and 4-Hydroxyquinolinones with Arylsulfonyl-Hydrazides and Selective Fluorescence Switch on Sensing of Cadmium(Ⅱ) Ion in Water[J]. Adv Synth Catal,2016,358(19):3050-3056.
[7]	Täubl A E,Langhans K,Kappe T,et al. Thermolytic Ring Closure Reactions of 4-Azido-3-Phenylsulfanyl- and 4-Azido-3-Phenylsulfonyl-2-Quinolones to 12H-Quinolino-[3,4-b][1,4] Benzothiazin-6(5H)-Ones[J]. J Heterocycl Chem,2002,39(6):1259-1264.
[8]	Schnell B,Kappe T.Sulfenylation of Heterocyclic 1,3-Dicarbonyl Compounds[J]. Monatsh Chem/Chem Mon,1999,130(9):1147-1157.
[9]	Guo T,Wei X N.Ammonium Iodide-Mediated Sulfenylation of 4-Hydroxycoumarins or 4-Hydroxyquinolinones with a Sulfonyl Chloride as a Sulfur Source[J]. Synlett,2017,28(18):2499-2504.
[10]	Stein A,Alves D,Rocha J,et al. Copper Iodide-Catalyzed Cyclization of (Z)-Chalcogenoenynes[J]. Org Lett,2008,10(21):4983-4986.
[11]	Guo T,Wang H.Copper-Mediated Direct Sulfenylation of 4-Hydroxyquinolinones and 4-Hydroxypyridones with Aryl Thiols via a C-H Functionalization Process[J]. Synlett,2017,28(14):1845-1851.
[12]	Zhang J,Liao Y,Deng J,et al. Oxidative Dual C-H Thiolation of Imidazopyridines with Ethers or Alkanes Using Elemental Sulphur[J]. Chem Commun,2017,53(55):7784-7787.