Ultrasound-assisted tandem synthesis of tri- and tetra-substituted pyrrole-2-carbonitriles from alkenes, TMSCN and N,N-disubstituted formamides

被引：39

作者：

Gui, Qing-Wen ^{[1
]}

Teng, Fan ^{[1
]}

Ying, Sheng-Neng ^{[1
]}

Liu, Yang ^{[1
]}

Guo, Tao ^{[1
]}

Tang, Jian-Xin ^{[2
]}

Chen, Jin-Yang ^{[3
]}

Cao, Zhong ^{[3
]}

He, Wei-Min ^{[3
]}

机构：

[1] Hunan Agr Univ, Coll Chem & Mat Sci, Changsha 410128, Peoples R China

[2] Hunan Univ Technol, Sch Life Sci & Chem, Zhuzhou 412007, Peoples R China

[3] Changsha Univ Sci & Technol, Hunan Prov Key Lab Mat Protect Elect Power & Tran, Changsha 410114, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2020年 / 31卷 / 12期

关键词：

Green chemistry; Solvent-free; Tandem reaction; Dual role; Ultrasound; POLYSUBSTITUTED PYRROLES; RADICAL CYCLIZATION; MULTISUBSTITUTED PYRROLES; EFFICIENT SYNTHESIS; ANNULATION; OXIDATION; CF3SO2NA; CATALYST; STYRENES; SOLVENT;

D O I：

10.1016/j.cclet.2020.07.017

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An energy-saving and eco-friendly method for the efficient construction of various tri- and tetra-substituted pyrrolecarbonitriles through ultrasound-assisted multicomponent tandem reaction of readily available alkenes, TMSCN and N,N-disubstituted formamides within 40 min under metal-, solvent-free and mild conditions was developed. The dual role of iodine (catalyst and oxidant) notably simplified the reaction conditions and reduced the chemical waste generated (C) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

引用

页码：3241 / 3244

页数：4

共 73 条

[1] Metal-Free Catalytic Synthesis of Thiocarbamates Using Sodium Sulfinates as the Sulfur Source
Bao, Pengli
Wang, Leilei
Yue, Huilan
Shao, Yun
Wen, Jiangwei
Yang, Daoshan
Zhao, Xiaohui
Wang, Hua
Wei, Wei
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (05) : 2976 - 2983
[2] Clean preparation of S-thiocarbamates with in situ generated hydroxide in 2-methyltetrahydrofuran
Bao, Wen-Hu
Wang, Zheng
Tang, Xiao
Zhang, Yun-Fu
Tan, Jia-Xi
Zhu, Qin
Cao, Zhong
Lin, Ying-Wu
He, Wei-Min
[J]. CHINESE CHEMICAL LETTERS, 2019, 30 (12) : 2259 - 2262
[3] The concept of dual roles design in clean organic preparation
Cao, Zhong
Zhu, Qin
Lin, Ying-Wu
He, Wei-Min
[J]. CHINESE CHEMICAL LETTERS, 2019, 30 (12) : 2132 - 2138
[4] Switchable Reactivity between Vinyl Azides and Terminal Alkyne by Nano Copper Catalysis
Cen, Jinghe
Wu, Yaodan
Li, Jianxiao
Huang, Liangbin
Wu, Wanqing
Zhu, Zhongzhi
Yang, Shaorong
Jiang, Huanfeng
[J]. ORGANIC LETTERS, 2019, 21 (07) : 2090 - 2094
[5] Ultrasound and microwave irradiation: contributions of alternative physicochemical activation methods to Green Chemistry
Chatel, Gregory
Varma, Rajender S.
[J]. GREEN CHEMISTRY, 2019, 21 (22) : 6043 - 6050
[6] External Reductant-Free Palladium-Catalyzed Reductive Insertion of Isocyanide: Synthesis of Polysubstituted Pyrroles and Its Applications as a Cysteine Probe
Chen, Dianpeng
Shan, Yingying
Li, Jianming
You, Jinmao
Sun, Xuejun
Qiu, Guanyinsheng
[J]. ORGANIC LETTERS, 2019, 21 (11) : 4044 - 4048
[7] Metal-free synthesis of 1,2,3-benzotriazines
Chen, Jin-Yang
Lin, Ying-Wu
He, Wei-Min
[J]. CHINESE CHEMICAL LETTERS, 2020, 31 (12) : 2989 - 2990
[8] Electrochemical Synthesis of α-Ketoamides under Catalyst-, Oxidant-, and Electrolyte-Free Conditions
Chen, Jin-Yang
Wu, Hong-Yu
Gui, Qing-Wen
Han, Xiao-Ran
Wu, Yan
Du, Kui
Cao, Zhong
Lin, Ying-Wu
He, Wei-Min
[J]. ORGANIC LETTERS, 2020, 22 (06) : 2206 - 2209
[9] Synthesis of Polysubstituted Pyrroles through a Formal [4+11 Cycloaddition/E1 cb Elimination/Aromatization Sequence of Sulfur Ylides and α,β-Unsaturated Imines
Cheng, Bei-Yi
Wang, Ya-Ni
Li, Tian-Ren
Lu, Liang-Qiu
Xiao, Wen-Jing
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (23) : 12134 - 12140
[10] Base-promoted ring-closing carbonyl-allene metathesis for the synthesis of 2,4-disubstituted pyrroles
Cheng, Guolin
Lv, Weiwei
Xue, Lulu
[J]. GREEN CHEMISTRY, 2018, 20 (19) : 4414 - 4417

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