Elemental sulfur mediated synthesis of benzoxazoles, benzothiazoles and quinoxalines via decarboxylative coupling of 2-hydroxy/mercapto/amino-anilines with cinnamic acids

被引:19
作者
Guntreddi, Tirumaleswararao [1 ]
Vanjari, Rajeshwer [1 ]
Kumar, Saurabh [1 ]
Singh, Rahul [1 ]
Singh, Neetu [1 ]
Kumar, Promod [1 ]
Singh, Krishna Nand [1 ]
机构
[1] Banaras Hindu Univ, Dept Chem, Ctr Adv Study, Inst Sci, Varanasi 221005, Uttar Pradesh, India
关键词
ONE-POT SYNTHESIS; COPPER-CATALYZED SYNTHESIS; C-H FUNCTIONALIZATION; OXIDATIVE CYCLIZATION; EFFICIENT SYNTHESIS; CARBOXYLIC-ACIDS; BOND FORMATION; AQUEOUS-MEDIA; DERIVATIVES; STRATEGY;
D O I
10.1039/c6ra17491d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An easy and practical method has been developed for the synthesis of 2-benzylbenzoxazoles and 2-benzylbenzothiazoles using sulfur mediated decarboxylative coupling of cinnamic acids with 2-hydroxyanilines and 2-mercaptoanilines respectively under metal- and solvent-free conditions. However, the reaction of 2-aminoanilines with cinnamic acids leads to the formation of 2-arylquinoxalines under the same set of reaction conditions. The transformation is versatile and compatible with a number of functional groups.
引用
收藏
页码:81013 / 81016
页数:4
相关论文
共 61 条
[1]   C-H Bond Arylations and Benzylations on Oxazol(in)es with a Palladium Catalyst of a Secondary Phosphine Oxide [J].
Ackermann, Lutz ;
Barfuesser, Sebastian ;
Kornhaass, Christoph ;
Kapdi, Anant R. .
ORGANIC LETTERS, 2011, 13 (12) :3082-3085
[2]   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
[3]   New approaches for decarboxylative biaryl coupling [J].
Baudoin, Olivier .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (09) :1373-1375
[4]   Decarboxylative functionalization of cinnamic acids [J].
Borah, Arun Jyoti ;
Yan, Guobing .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (30) :8094-8115
[5]   Novel Cyano- and Amidinobenzothiazole Derivatives: Synthesis, Antitumor Evaluation, and X-ray and Quantitative Structure-Activity Relationship (QSAR) Analysis [J].
Caleta, Irena ;
Kralj, Marijeta ;
Marjanovic, Marko ;
Bertosa, Branimir ;
Tomic, Sanja ;
Pavlovic, Gordana ;
Pavelic, Kresimir ;
Karminski-Zamola, Grace .
JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (06) :1744-1756
[6]   Oxidation of alkynes using PdCl2/CuCl2 in PEG as a recyclable catalytic system: one-pot synthesis of quinoxalines [J].
Chandrasekhar, S. ;
Reddy, N. Kesava ;
Kumar, V. Praveen .
TETRAHEDRON LETTERS, 2010, 51 (28) :3623-3625
[7]   Copper-Catalyzed Cascade Cycloamination of α-Csp3-H Bond of N-Aryl Ketimines with Azides: Access to Quinoxalines [J].
Chen, Tengfei ;
Chen, Xun ;
Wei, Jun ;
Lin, Dongen ;
Xie, Ying ;
Zeng, Wei .
ORGANIC LETTERS, 2016, 18 (09) :2078-2081
[8]   A new ruthenium-catalyzed approach for quinoxalines from o-phenylenediamines and vicinal-diols [J].
Cho, Chan Sik ;
Oh, Sung Gi .
TETRAHEDRON LETTERS, 2006, 47 (32) :5633-5636
[9]   STRUCTURE REVISION OF ANTIBIOTIC ECHINOMYCIN [J].
DELL, A ;
WILLIAMS, DH ;
MORRIS, HR ;
SMITH, GA ;
FEENEY, J ;
ROBERTS, GCK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (09) :2497-2502
[10]   A novel and practical synthesis of 2-benzoylbenzothiazoles and 2-benzylbenzothiazoles [J].
Fan, Xuesen ;
He, Yan ;
Wang, Yangyang ;
Xue, Zaikun ;
Zhang, Xinying ;
Wang, Jianji .
TETRAHEDRON LETTERS, 2011, 52 (08) :899-902