Electrochemical oxidative annulation of amines and aldehydes or ketones to synthesize polysubstituted pyrroles

被引:39
作者
Gao, Xinlong [1 ]
Wang, Pan [1 ]
Wang, Qingqing [1 ]
Chen, Jingting [1 ]
Lei, Aiwen [1 ,2 ]
机构
[1] Wuhan Univ, Coll Chem & Mol Sci, IAS, Wuhan 430072, Hubei, Peoples R China
[2] Jiangxi Normal Univ, Natl Res Ctr Carbohydrate Synth, Nanchang 330022, Jiangxi, Peoples R China
基金
中国国家自然科学基金;
关键词
H BOND FUNCTIONALIZATION; PAAL-KNORR SYNTHESIS; MEDIATED SYNTHESIS; CONCISE SYNTHESES; ELECTROSYNTHESIS; LAMELLARINS; DERIVATIVES; ALKALOIDS; ALKENES;
D O I
10.1039/c9gc02118c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A general and practical protocol to synthesize polysubstituted pyrroles has been established by electrooxidative annulation of amines and aldehydes or ketones. In an undivided cell, arylacetaldehydes and primary amines can participate in this transformation smoothly to furnish beta-substituted pyrroles under external oxidant-free conditions. Tetrasubstituted pyrroles could be obtained efficiently by using imines as substrates. In addition, this reaction can be extended to gram levels; the final products can also undergo late stage functionalization.
引用
收藏
页码:4941 / 4945
页数:5
相关论文
共 61 条
[1]   Pyrrole: An insight into recent pharmacological advances with structure activity relationship [J].
Ahmad, Shujauddin ;
Alam, Ozair ;
Naim, Mohd. Javed ;
Shaquiquzzaman, Mohammad ;
Alam, M. Mumtaz ;
Iqbal, Muzaffar .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 157 :527-561
[2]   INTERMEDIATES IN THE PAAL-KNORR SYNTHESIS OF PYRROLES [J].
AMARNATH, V ;
ANTHONY, DC ;
AMARNATH, K ;
VALENTINE, WM ;
WETTERAU, LA ;
GRAHAM, DG .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6924-6931
[3]   Chemoselective Synthesis of 1-Substituted 4-Amino-2-(trifluoromethyl)-1H-pyrroles through the Heterocyclization Reaction of 4-Methoxy-5-bromo-1,1,1-trifluoropent-3-en-2-ones with Amines [J].
Aquino, Estefania da C. ;
Leonel, Guilherme ;
Gariboti, Vanessa C. ;
Frizzo, Clarissa P. ;
Martins, Marcos A. P. ;
Bonacorso, Helio G. ;
Zanatta, Nilo .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (24) :12453-12459
[4]   Paal-Knorr synthesis of pyrroles: from conventional to green synthesis [J].
Balakrishna, Avula ;
Aguiar, Antonio ;
Sobral, Pedro J. M. ;
Wani, Mohmmad Younus ;
Almeida e Silva, Joana ;
Sobral, Abilio J. F. N. .
CATALYSIS REVIEWS-SCIENCE AND ENGINEERING, 2019, 61 (01) :84-110
[5]   Synthesis of rhazinicine by a metal-catalyzed C-H bond functionalization strategy [J].
Beck, Elizabeth M. ;
Hatley, Richard ;
Gaunt, Matthew J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (16) :3004-3007
[6]   Dehydrogenative reagent-free annulation of alkenes with diols for the synthesis of saturated O-heterocycles [J].
Cai, Chen-Yan ;
Xu, Hai-Chao .
NATURE COMMUNICATIONS, 2018, 9
[7]   Palladium-Catalyzed Reaction of Arylamine and Diarylacetylene: Solvent-Controlled Construction of 2,3-Diarylindoles and Pentaarylpyrroles [J].
Chen, Xiaopeng ;
Li, Xihui ;
Wang, Ningning ;
Jin, Jisong ;
Lu, Ping ;
Wang, Yanguang .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (23) :4380-4386
[8]   Study on photochromism of diarylethenes with a 2,5-dihydropyrrole bridging unit: A convenient preparation of 3,4-diarylpyrroles from 3,4-diaryl-2,5-dihydropyrroles [J].
Chen, Y ;
Zeng, DX ;
Xie, N ;
Dang, YZ .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13) :5001-5005
[9]   Effect of Substituent Position on the Photophysical Properties of Triphenylpyrrole Isomers [J].
Dong, Lichao ;
Shang, Guojun ;
Shi, Jianbing ;
Zhi, Junge ;
Tong, Bin ;
Dong, Yuping .
JOURNAL OF PHYSICAL CHEMISTRY C, 2017, 121 (21) :11658-11664
[10]   Recent advances in the synthesis of pyrroles by multicomponent reactions [J].
Estevez, Veronica ;
Villacampa, Mercedes ;
Menendez, J. Carlos .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (13) :4633-4657