TEMPO-mediated aerobic oxidative synthesis of 2-aryl benzoxazoles via ring-opening of benzoxazoles with benzylamines

被引：4

作者：

Rao, Mugada Sugunakara ^{[1
]}

Hussain, Sahid ^{[1
]}

机构：

[1] Indian Inst Technol Patna, Dept Chem, Patna 801106, Bihar, India

来源：

SYNTHETIC COMMUNICATIONS | 2021年 / 51卷 / 17期

关键词：

Aerobic oxidation; amines; benzoxazoles; ring-opening; TEMPO; ONE-POT SYNTHESIS; C-H ARYLATION; INTRAMOLECULAR O-ARYLATION; CATALYZED DESULFITATIVE ARYLATION; PRIMARY ALIPHATIC-AMINES; SOLVENT-FREE CONDITIONS; ESTROGEN-RECEPTOR-BETA; METAL-FREE ARYLATION; HIGHLY EFFICIENT; 2-SUBSTITUTED BENZOXAZOLES;

D O I：

10.1080/00397911.2021.1949476

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient TEMPO-mediated system for aerobic oxidative synthesis of 2-aryl benzoxazoles from readily available benzoxazoles and primary benzylic and hetero benzylic amines is presented in one pot. The reaction proceeds through the ring-opening of benzoxazoles and is followed by oxidative condensation with benzylamines. These metal-free, straightforward reactions worked well with a wide range of substrates, yielding moderate to good yields under mild conditions using air as an external green oxidant.

引用

页码：2684 / 2694

页数：11

共 156 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]

[Anonymous], 2010, Angew. Chem

[5] Synthesis, antimicrobial activity and QSAR studies of 2,5-disubstituted benzoxazoles [J].

Arisoy, M. ;

Temiz-Arpaci, O. ;

Yildiz, I. ;

Kaynak-Onurdag, F. ;

Aki, E. ;

Yalcin, I. ;

Abbasoglu, U. .

SAR AND QSAR IN ENVIRONMENTAL RESEARCH, 2008, 19 (5-6) :589-612

[6] KF-Al2O3as a Base Heterogeneous Catalyst for the Synthesis of 2-Substituted Benzoxazoles and Benzothiazoles under Mild Reaction Conditions at Room Temperature [J].

Bahadorikhalili, Saeed ;

Sardarian, Ali Reza .

POLYCYCLIC AROMATIC COMPOUNDS, 2020, 40 (04) :990-997

[7] Highly efficient water-mediated approach to access benzazoles: metal catalyst and base-free synthesis of 2-substituted benzimidazoles, benzoxazoles, and benzothiazoles [J].

Bala, Manju ;

Verma, Praveen Kumar ;

Sharma, Deepika ;

Kumar, Neeraj ;

Singh, Bikram .

MOLECULAR DIVERSITY, 2015, 19 (02) :263-272

[8] Copper-catalysed intramolecular O-arylation of aryl chlorides and bromides:: a straightforward approach to benzo[d]oxazoles in water [J].

Barbero, Nekane ;

Carril, Monica ;

SanMartin, Raul ;

Dominguez, Esther .

TETRAHEDRON, 2007, 63 (42) :10425-10432

[9] Oxidative conversion of amines into benzoxazoles using hydrogen transfer catalysis [J].

Blacker, A. John ;

Farah, Mohamed M. ;

Marsden, Stephen P. ;

Saidi, Ourida ;

Williams, Jonathan M. J. .

TETRAHEDRON LETTERS, 2009, 50 (45) :6106-6109

[10] A Powerful Palladium-Catalyzed Multicomponent Process for the Preparation of Oxazolines and Benzoxazoles [J].

Boissarie, Patrick J. ;

Hamilton, Zoe E. ;

Lang, Stuart ;

Murphy, John A. ;

Suckling, Colin J. .

ORGANIC LETTERS, 2011, 13 (23) :6256-6259

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