Efficient Aerobic Oxidative Synthesis of 2-Substituted Benzoxazoles, Benzothiazoles, and Benzimidazoles Catalyzed by 4-Methoxy-TEMPO

被引：334

作者：

Chen, Yong-Xing ^{[1
,2
]}

Qian, Ling-Feng ^{[1
,2
]}

Zhang, Wei ^{[1
,2
]}

Han, Bing ^{[1
,2
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Lanzhou Univ, Dept Chem, Lanzhou 730000, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 48期

关键词：

aerobic oxidation; cyclization; heterocycles; synthetic methods;

D O I：

10.1002/anie.200803381

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Setting the TEMPO: The scheme shows the efficient aerobic synthesis of 2-substituted benzoxazoles, benzothiazoles, and benzimidazoles where 4-methoxy-2,2,6,6-tetramethyl-1-piperidinyloxy free radical (4-Methoxy-TEMPO) is used as the catalyst. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

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页码：9330 / 9333

页数：4

相关论文

共 43 条

[1] Neutron diffraction study of a phenol-nitroxide radical adduct: A structural model for hydrogen atom abstraction by peroxyl radicals from vitamin E and related phenolic antioxidants [J].

Ahrens, B ;

Davidson, MG ;

Forsyth, VT ;

Mahon, MF ;

Johnson, AL ;

Mason, SA ;

Price, RD ;

Raithby, PR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) :9164-9165

[2] A new method to study antioxidant capability:: Hydrogen transfer from phenols to a prefluorescent nitroxide [J].

Aliaga, C ;

Aspée, A ;

Scaiano, JC .

ORGANIC LETTERS, 2003, 5 (22) :4145-4148

[3] Hydrogen-transfer reactions from phenols to TEMPO prefluorescent probes in micellar systems [J].

Aliaga, Carolina ;

Juarez-Ruiz, Juan M. ;

Scaiano, J. C. ;

Aspee, Alexis .

ORGANIC LETTERS, 2008, 10 (11) :2147-2150

[4] A domino copper-catalyzed C-N and C-O cross-coupling for the conversion of primary amides into benzoxazoles [J].

Altenhoff, G ;

Glorius, F .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1661-1664

[5]

[Anonymous], ANGEW CHEM

[6] Media effects on antioxidant activities of phenols and catechols [J].

Barclay, LRC ;

Edwards, CE ;

Vinqvist, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (26) :6226-6231

[7] Synthesis, structure-activity relationships, and antitumor studies of 2-benzoxazolyl hydrazones derived from alpha-(N)-acyl heteroaromatics [J].

Easmon, Johnny ;

Purstinger, Gerhard ;

Thies, Katrin-Sofia ;

Heinisch, Gottfried ;

Hofmann, Johann .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (21) :6343-6350

[8] Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides [J].

Evindar, G ;

Batey, RA .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05) :1802-1808

[9]

Franchi P, 2002, CHEMPHYSCHEM, V3, P789, DOI 10.1002/1439-7641(20020916)3:9<789::AID-CPHC789>3.0.CO

[10]

2-Z

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