Palladium-Catalyzed Chemo- and Regioselective Oxidative Cross-Dehydrogenative Coupling of Acetanilides with Benzothiazole

被引:10
作者
Kianmehr, Ebrahim [1 ]
Fardpour, Maryam [1 ]
Kharat, Ali Nemati [1 ]
机构
[1] Univ Tehran, Coll Sci, Sch Chem, Tehran, Iran
关键词
Arylation; Cross-coupling; C-H activation; Dehydrogenation; Heterocycles; C-H BOND; CARBOXYLIC-ACIDS; DIRECT ARYLATION; ANTITUMOR BENZOTHIAZOLES; ORTHO-HETEROARYLATION; BIOLOGICAL-PROPERTIES; COPPER; AZOLES; POTENT; BENZOXAZOLES;
D O I
10.1002/ejoc.201700290
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical, versatile, and efficient method for the palladium-catalyzed direct heteroarylation of acetanilides was developed. In this method, a wide range of acetanilides bearing electron-donating and electron-withdrawing groups are well tolerated, and the desired 2-arylbenzothiazoles are generated in good to high yields through a cross-dehydrogenative coupling process.
引用
收藏
页码:3017 / 3021
页数:5
相关论文
共 65 条
[1]   Palladium-Catalyzed Regioselective C-H Bond Arylations of Benzoxazoles and Benzothiazoles at the C7 Position [J].
Abdellaoui, Fatma ;
Youssef, Chiraz ;
Ben Ammar, Hamed ;
Roisnel, Thierry ;
Soule, Jean-Francois ;
Doucet, Henri .
ACS CATALYSIS, 2016, 6 (07) :4248-4252
[2]  
Ackermann L, 2009, MODERN ARYLATION METHODS, P1
[3]   Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648) [J].
Aiello, Stefania ;
Wells, Geoffrey ;
Stone, Erica L. ;
Kadri, Hachemi ;
Bazzi, Rana ;
Bell, David R. ;
Stevens, Malcolm F. G. ;
Matthews, Charles S. ;
Bradshaw, Tracey D. ;
Westwell, Andrew D. .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (16) :5135-5139
[4]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[5]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
[6]   Exploration of in vitro time point quantitative evaluation of newly synthesized benzimidazole and benzothiazole derivatives as potential antibacterial agents [J].
Bandyopadhyay, Prabal ;
Sathe, Manisha ;
Ponmariappan, S. ;
Sharma, Arti ;
Sharma, Pratibha ;
Srivastava, A. K. ;
Kaushik, M. P. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (24) :7306-7309
[7]   Regioselectivity in palladium-catalysed direct arylation of 5-membered ring heteroaromatics [J].
Bheeter, Charles Beromeo ;
Chen, Lu ;
Soule, Jean-Francois ;
Doucet, Henri .
CATALYSIS SCIENCE & TECHNOLOGY, 2016, 6 (07) :2005-2049
[8]   The discovery of the potent and selective antitumour agent 2-(4-amino-3-methylphenyl)benzothiazole (DF 203) and related compounds [J].
Bradshaw, TD ;
Stevens, MFG ;
Westwell, AD .
CURRENT MEDICINAL CHEMISTRY, 2001, 8 (02) :203-210
[9]   Palladium-catalyzed desulfitative C-H arylation of azoles with sodium sulfinates [J].
Chen, Ru ;
Liu, Saiwen ;
Liu, Xinhua ;
Yang, Luo ;
Deng, Guo-Jun .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (22) :7675-7679
[10]   Palladium-catalyzed oxidative C-H/C-H cross-coupling of benzothiazoles with thiophenes and thiazoles [J].
Chen, Xuxing ;
Huang, Xiaojing ;
He, Qian ;
Xie, Yuyuan ;
Yang, Chunhao .
CHEMICAL COMMUNICATIONS, 2014, 50 (30) :3996-3999