Synthesis of Substituted Oxazoles by Visible-Light Photocatalysis

被引：80

作者：

Chatterjee, Tanmay ^{[1
]}

Cho, Ji Young ^{[1
]}

Cho, Eun Jin ^{[1
]}

机构：

[1] Chung Ang Univ, Dept Chem, 84 Heukseok Ro, Seoul 06974, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 16期

基金：

新加坡国家研究基金会;

关键词：

DOMINO OXIDATIVE CYCLIZATION; POLY(ARYL ETHER OXAZOLE)S; 2,5-DISUBSTITUTED OXAZOLES; BIOLOGICAL EVALUATION; METAL-FREE; PHOTOREDOX; CHEMISTRY; AZOLES; DERIVATIVES; ARYLATION;

D O I：

10.1021/acs.joc.6b00989

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and practical method for the synthesis of substituted oxazoles has been developed using readily available alpha-bromoketones and benzylamines by visible-light photocatalysis at room temperature. The process, which requires 1 mol % of [Ru(bpy)(3)]Cl-2 photocatalyst with K3PO4 and CCl3Br, is effective for accessing a variety of valuable oxazole compounds. The synthetic utility of our protocol was also demonstrated by preparing a natural prochict, texaline.

引用

页码：6995 / 7000

页数：6

共 50 条

[1]

[Anonymous], 2004, OXAZOLES SYNTHESIS B

[2] Mild Palladium-Catalyzed Regioselective Direct Arylation of Azoles Promoted by Tetrabutylammonium Acetate [J].

Bellina, Fabio ;

Lessi, Marco ;

Manzini, Chiara .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (25) :5621-5630

[3] Ligandless microwave-assisted Pd/Cu-catalyzed direct arylation of oxazoles [J].

Besselievre, Francois ;

Mahuteau-Betzer, Florence ;

Grierson, David S. ;

Piguel, Sandrine .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (08) :3278-3280

[4] Design, synthesis and biological evaluation of bis(hydroxyphenyl) azoles as potent and selective non-steroidal inhibitors of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) for the treatment of estrogen-dependent diseases [J].

Bey, Emmanuel ;

Marchais-Oberwinkler, Sandrine ;

Kruchten, Patricia ;

Frotscher, Martin ;

Werth, Ruth ;

Oster, Alexander ;

Alguel, Oztekin ;

Neugebauer, Alexander ;

Hartmann, Rolf W. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (12) :6423-6435

[5] The chemistry of pseudomonic acid .15. Synthesis and antibacterial activity of a series of 5-alkyl, 5-alkenyl, and 5-heterosubstituted oxazoles [J].

Brown, P ;

Davies, DT ;

OHanlon, PJ ;

Wilson, JM .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (02) :446-457

[6] Regioselective Formation of 2,5-Disubstituted Oxazoles Via Copper(I)-Catalyzed Cycloaddition of Acyl Azides and 1-Alkynes [J].

Cano, Israel ;

Alvares, Eleuterio ;

Carmen Nicasio, M. ;

Perez, Pedro J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (02) :191-193

[7] Visible-light-induced regioselective synthesis of polyheteroaromatic compounds [J].

Chatterjee, Tanmay ;

Choi, Myung Gil ;

Kim, Jun ;

Chang, Suk-Kyu ;

Cho, Eun Jin .

CHEMICAL COMMUNICATIONS, 2016, 52 (22) :4203-4206

[8] Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C-H Functionalization [J].

Cheung, Chi Wai ;

Buchwald, Stephen L. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (17) :7526-7537

[9] Synthesis of Carbazoles by a Merged Visible Light Photoredox and Palladium-Catalyzed Process [J].

Choi, Sungkyu ;

Chatterjee, Tanmay ;

Choi, Won Joon ;

You, Youngmin ;

Cho, Eun Jin .

ACS CATALYSIS, 2015, 5 (08) :4796-4802

[10]

DOMINGUEZ X A, 1988, Heterocycles (Tokyo), V27, P35

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