Transition-metal free 2-arylbenzoxazole formation from aryl amides and cyclohexanones

被引:57
作者
Cao, Xiangxiang [1 ]
Cheng, Xiufang [1 ]
Bai, Yang [1 ]
Liu, Saiwen [1 ]
Deng, Guo-Jun [1 ,2 ]
机构
[1] Xiangtan Univ, Coll Chem, Minist Educ, Key Lab Environm Friendly Chem & Applicat, Xiangtan 411105, Peoples R China
[2] Chinese Acad Sci, Inst Chem, Key Lab Mol Recognit & Funct, Beijing 100080, Peoples R China
基金
中国国家自然科学基金; 高等学校博士学科点专项科研基金;
关键词
CATALYZED DIRECT ARYLATION; C-H ARYLATION; AEROBIC DEHYDROGENATION; ARYLBORONIC ACIDS; BOND FORMATION; BENZOXAZOLES; HETEROARENES; EFFICIENT; AZOLES; BENZOTHIAZOLES;
D O I
10.1039/c4gc01572j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A transition-metal-free method for the synthesis of 2-arylbenzoxazoles from readily available cyclohexanones and benzamides is described. The combined use of KI, p-TsOH and DMSO significantly improved the reaction yields. Non-aromatic cyclohexanones were smoothly dehydrogenated and acted as the aryl source using oxygen as the oxidant.
引用
收藏
页码:4644 / 4648
页数:5
相关论文
共 60 条
[1]   Palladium-Catalyzed Direct Arylations of Heteroarenes with Tosylates and Mesylates [J].
Ackermann, Lutz ;
Althammer, Andreas ;
Fenner, Sabine .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) :201-204
[2]   DEHYDROGENATION AND COUPLING REACTIONS IN PRESENCE OF IODINE AND MOLTEN-SALT HYDROGEN IODIDE ACCEPTORS [J].
ADAMS, CT ;
BRANDENBERGER, SG ;
DUBOIS, JB ;
MILL, GS ;
NAGER, M ;
RICHARDSON, DB .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (01) :1-6
[3]   AROMATIC BENZENE COMPOUNDS FROM ACYCLIC PRECURSORS [J].
BAMFIELD, P ;
GORDON, PF .
CHEMICAL SOCIETY REVIEWS, 1984, 13 (04) :441-488
[4]   Synthesis of 2-substituted-benzothiazoles by palladium-catalyzed intramolecular cyclization of o-bromophenylthioureas and o-bromophenylthioamides [J].
Benedí, C ;
Bravo, F ;
Uriz, P ;
Fernández, E ;
Claver, C ;
Castillón, S .
TETRAHEDRON LETTERS, 2003, 44 (32) :6073-6077
[5]   One-pot preparation of 2-(Alkyl)arylbenzothiazoles from the corresponding o-halobenzanilides [J].
Bernardi, Dan ;
Ba, Lalla Aiecha ;
Kirsch, Gilbert .
SYNLETT, 2007, (13) :2121-2123
[6]   Iron-catalyzed intramolecular O-arylation:: Synthesis of 2-aryl benzoxazoles [J].
Bonnamour, Julien ;
Bolm, Carsten .
ORGANIC LETTERS, 2008, 10 (13) :2665-2667
[7]   Dess-Martin Periodinane Mediated Intramolecular Cyclization of Phenolic Azomethines: A Solution-Phase Strategy toward Benzoxazoles and Benzothiazoles [J].
Bose, D. Subhas ;
Idrees, Mohd .
SYNTHESIS-STUTTGART, 2010, (03) :398-402
[8]  
Buckle D.R., 2010, Encyclopedia of Reagents for Organic Synthesis
[9]   Palladium-Catalyzed Direct Arylation of Indoles with Cyclohexanones [J].
Chen, Shanping ;
Liao, Yunfeng ;
Zhao, Feng ;
Qi, Hongrui ;
Liu, Saiwen ;
Deng, Guo-Jun .
ORGANIC LETTERS, 2014, 16 (06) :1618-1621
[10]   Efficient Aerobic Oxidative Synthesis of 2-Substituted Benzoxazoles, Benzothiazoles, and Benzimidazoles Catalyzed by 4-Methoxy-TEMPO [J].
Chen, Yong-Xing ;
Qian, Ling-Feng ;
Zhang, Wei ;
Han, Bing .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (48) :9330-9333