Convenient Synthesis of Highly Functionalized α-Cyanothiophene Derivatives via Three-component Reaction

Chem. J. Chinese Universities

• 研究论文 • Previous Articles Next Articles

Convenient Synthesis of Highly Functionalized α-Cyanothiophene Derivatives via Three-component Reaction

GAO Yu-Xiang^1,2, SUN Jun³, XU Xian-Xiu^1*, LIU Qun¹

1. Department of Chemistry, Northeast Normal University, Changchun 130024, China;
2. Department of Chemistry, Tonghua Normal University, Tonghua 134002, China;
3. Jilin City Bureau Quality and Technical Supervision, Jilin 132001, China

Received:2008-04-23 Revised:1900-01-01 Online:2009-01-10 Published:2009-01-10
Contact: XU Xian-Xiu

Abstract

Abstract: A convenient one-pot synthesis of highly functionalized α-cyanothiophene derivatives(4) by three-component reactions was developed. In the presence of K₂CO₃, 1,3-dicarbonyl compounds 1 reacted with CS₂(2) and bromoacetonitrile(3) resulted in the formation of functionalized α-cyanothiophenes(4) in high yields. The simplicity of execution, mild conditions, ready availability of substrates and high yields, make this synthetic strategy considerably attractive for academic research and practical applications.

Key words: Three-component reactions, α-Cyanothiophene, 1,3-Dicarbonyl compounds, α-Oxo ketene-(S,S)-acetals

CLC Number:

O621.3

TrendMD:

GAO Yu-Xiang^1,2, SUN Jun³, XU Xian-Xiu^1*, LIU Qun¹. Convenient Synthesis of Highly Functionalized α-Cyanothiophene Derivatives via Three-component Reaction[J]. Chem. J. Chinese Universities, doi: .

[1]	LIN Junxu, XI Zhiwei, LI Zhiping, WANG Yingchun. Palladium Catalyzed Selective Synthesis of Pyrrolofuran Derivatives and Carbamates from Propargylic Alcohols and Tert butyl isonitrile#br# [J]. Chem. J. Chinese Universities, 0, (): 20220473.
[2]	GUO Zhiqiang, YANG Boru, XI Chanjuan. Recent Advances in Reductive Functionalization of Carbon Dioxide with Borohydride Reagents [J]. Chem. J. Chinese Universities, 2022, 43(7): 20220199.
[3]	ZHANG Zhen, DENG Yu, ZHANG Qinfang, YU Dagang. Visible Light-driven Carboxylation with CO₂ [J]. Chem. J. Chinese Universities, 2022, 43(7): 20220255.
[4]	YU Jing, WU Chao, LI Chenyang, CHEN Danfeng, DING Liuyue, MA Xiantao. Catalyst-free and Highly Efficient O-Silylation of Alcohols and Phenols [J]. Chem. J. Chinese Universities, 2022, 43(2): 20210588.
[5]	HU Chuanchuan, PANG Jingxiang, HE Chuangchuang, LI Wei, SUN Shutao. Sc（OTf）₃ Catalyzed 1，6-Conjugate Allylation of δ-CN p-QMs： Synthesis of Allyl Substituted Diarylacetonitrile Compounds [J]. Chem. J. Chinese Universities, 2021, 42(9): 2805.
[6]	LIU Huazheng, PAN Xiaoguang, LI Hua, WAN Renzhong, LIU Xigong. Na₂CO₃-catalyzed 1，6-Conjugate Addition of Trimethylsilyl Azide to δ-CF₃-δ-Aryl-disubstituted Para-Quinone Methides： Efficient Construction of Diarylmethanes Bearing CF₃- and N₃-Substituted Quaternary Stereocenters [J]. Chem. J. Chinese Universities, 2021, 42(9): 2772.
[7]	GUO Yang, LIN Kai, XIE Kaiqiang, LIU Sheng. Novel Approach to Isatins via Pd-Cu Catalyzed Oxidative Transformation [J]. Chem. J. Chinese Universities, 2021, 42(9): 2798.
[8]	LIN Junjie, WANG Shuang, LI Weiqiang, CUI Xin, HUANG Chao. Efficient Synthesis of Pyridine ［2，3-d］pyrimidine Derivatives by Catalyst-free Tandem Cyclization Under Microwave Irradiation [J]. Chem. J. Chinese Universities, 2020, 41(12): 2749.
[9]	ZHOU Jinlong, LIU Xiaolong, FU Yao. Visible-light-induced Selective Oxidation of Alcohols [J]. Chem. J. Chinese Universities, 2020, 41(11): 2435.
[10]	ZHANG Shuxin, FENG Yu, FAN Qinghua. Progress of Transition Metal⁃catalyzed Asymmetric Hydrogenation in China^† [J]. Chem. J. Chinese Universities, 2020, 41(10): 2107.
[11]	QIN Wenbing, LIN Weifeng, LI Xin, XIONG Wei, LIU Guokai. Difluoromethylation of Dicyanoalkylidenes by Electrophilic S-（Difluoromethyl）sulfonium Salt： Efficient Construction of Difluoromethylated All-carbon-substituted Centers^† [J]. Chem. J. Chinese Universities, 2020, 41(10): 2230.
[12]	WANG Yang, WANG Sidi, TANG Shaokun. Synthesis and Characterization of Imine-based Covalent Organic Framework(COF-LZU1) in Supercritical Carbon Dioxide [J]. Chem. J. Chinese Universities, 2020, 41(8): 1792.
[13]	XU Wenyi,FENG Yisi. Oxidative Trifluoromethylation of CF₃SO₂Na with Olefins Mediated by Diacetyl^† [J]. Chem. J. Chinese Universities, 2020, 41(7): 1567.
[14]	HUANG Mingyao, ZHU Shoufei. Recent Advances of Catalytic Asymmetric C—B Bond Forming Reactions^† [J]. Chem. J. Chinese Universities, 2020, 41(7): 1426.
[15]	SUN Mengying,Lü Jingchun,XU Hong,ZHANG Linping,ZHONG Yi,CHEN Zhize,SUI Xiaofeng,MAO Zhiping. Synthesis and Electrochromic Performance of Phosphazene-viologen Polymer ^† [J]. Chem. J. Chinese Universities, 2020, 41(6): 1399.

Convenient Synthesis of Highly Functionalized α-Cyanothiophene Derivatives via Three-component Reaction

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments