Visible Light-Promoted Three-Component Tandem Annulation for the Synthesis of 2-Iminothiazolidin-4-ones

被引：39

作者：

Guo, Wei ^{[1
]}

Zhao, Mingming ^{[1
]}

Tan, Wen ^{[1
]}

Zheng, Lvyin ^{[1
]}

Tao, Kailiang ^{[1
]}

Liu, Lingxiu ^{[1
]}

Wang, Xinyu ^{[1
]}

Chen, Deliang ^{[1
]}

Fan, Xiaolin ^{[1
]}

机构：

[1] Gannan Normal Univ, Key Lab Organopharmaceut Chem Jiangxi Prov, Ganzhou 341000, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 03期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; HETEROCYCLIC PHOTOCHEMISTRY; PHOTOREDOX CATALYSIS; DRIVEN; PHOTOCATALYSIS; REARRANGEMENT; DERIVATIVES; SELECTIVITY; GENERATION; COMPLEXES;

D O I：

10.1021/acs.joc.7b02940

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Described is a visible light-promoted three-component tandem annulation of amines, aryl/alkyl isothiocyanates, and alpha-bromoesters to form 2-iminothiazolidin-4-ones in the absence of metal and photocatalyst at room temperature. This [1 + 2 + 2] cyclization strategy involves visible light-promoted C-S/C-N bond formation and features a powerful approach to the synthesis of 2-iminothiazolidin-4-ones with broad substrate scope, excellent functional group tolerance, mild reaction conditions, step-economy, and simple operation, which also has potential applications in the pharmaceutical industry. UV vis spectroscopy indicates that an in situ-generated H-bonding electron donor acceptor (EDA) complex probably acts as the photocatalyst, facilitating the reaction process.

引用

页码：1402 / 1413

页数：12

共 60 条

[1]

Arceo E, 2013, NAT CHEM, V5, P750, DOI [10.1038/NCHEM.1727, 10.1038/nchem.1727]

[2] Design, synthesis and biological evaluation of 5-benzylidene-2-iminothiazolidin-4-ones as selective GSK-3β inhibitors [J].

Arfeen, Minhajul ;

Bhagat, Shweta ;

Patel, Rahul ;

Prasad, Shivcharan ;

Roy, Ipsita ;

Chakraborti, Asit K. ;

Bharatam, Prasad V. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 121 :727-736

[3] Multiple-component condensation strategies for combinatorial library synthesis [J].

Armstrong, RW ;

Combs, AP ;

Tempest, PA ;

Brown, SD ;

Keating, TA .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :123-131

[4] An Efficient Synthesis of 3-(3-benzyl-2-(phenylimino)-2,3-dihydrothiazol-4-yl)-6-methyl-4-(2-oxo-2-phenylethoxy)-3,4-dihydro-2H-pyran-2-one Derivatives via Multi-Component Approach [J].

Bade, Thirupaiah ;

Vedula, Rajeswar Rao .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (06) :1883-1886

[5] Photochemical Perfluoroalkylation with Pyridine N-Oxides: Mechanistic Insights and Performance on a Kilogram Scale [J].

Beatty, Joel W. ;

Douglas, James J. ;

Miller, Richard ;

McAtee, Rory C. ;

Cole, Kevin P. ;

Stephenson, Corey R. J. .

CHEM, 2016, 1 (03) :456-472

[6] An extremely efficient three-component reaction of aldehydes/ketones, amines, and phosphites (Kabachnik-Fields reaction) for the synthesis of α-aminophosphonates catalyzed by magnesium perchlorate [J].

Bhagat, Srikant ;

Chakraborti, Asit K. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1263-1270

[7] N-Acylbenzenesulfonamide Dihydro-1,3,4-oxadiazole Hybrids: Seeking Selectivity toward Carbonic Anhydrase Isoforms [J].

Bianco, Giulia ;

Meleddu, Rita ;

Distinto, Simona ;

Cottiglia, Filippo ;

Gaspari, Marco ;

Melis, Claudia ;

Corona, Angela ;

Angius, Rossella ;

Angeli, Andrea ;

Taverna, Domenico ;

Alcaro, Stefano ;

Leitans, Janis ;

Kazaks, Andris ;

Tars, Kaspars ;

Supuran, Claudiu T. ;

Maccioni, Elias .

ACS MEDICINAL CHEMISTRY LETTERS, 2017, 8 (08) :792-796

[8] 2-Imino-thiazolidin-4-one Derivatives as Potent, Orally Active S1P1 Receptor Agonists [J].

Bolli, Martin H. ;

Abele, Stefan ;

Binkert, Christoph ;

Bravo, Roberto ;

Buchmann, Stephan ;

Bur, Daniel ;

Gatfield, John ;

Hess, Patrick ;

Kohl, Christopher ;

Mangold, Celine ;

Mathys, Boris ;

Menyhart, Katalin ;

Mueller, Claus ;

Nayler, Oliver ;

Scherz, Michael ;

Schmidt, Gunther ;

Sippel, Virginie ;

Steiner, Beat ;

Strasser, Daniel ;

Treiber, Alexander ;

Weller, Thomas .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (10) :4198-4211

[9] Enantioselective Catalysis of Photochemical Reactions [J].

Brimioulle, Richard ;

Lenhart, Dominik ;

Maturi, Mark M. ;

Bach, Thorsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (13) :3872-3890

[10] A planning strategy for diversity-oriented synthesis [J].

Burke, MD ;

Schreiber, SL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (01) :46-58

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