1-(Hydroxymethyl)-1H-benzotriazole: An Efficient Ligand for Copper-Catalyzed Ullmann-Type Coupling Reaction Leading to Expeditious Synthesis of Diverse Benzoxazoles and Benzothiazoles

被引:7
作者
Singh, Mala [1 ]
Bose, Priyanka [1 ]
Singh, Anoop S. [1 ]
Tiwari, Vinod K. [1 ]
机构
[1] Banaras Hindu Univ, Inst Sci, Dept Chem, Varanasi 221005, Uttar Pradesh, India
关键词
Benzotriazole; Benzothiazole; Benzoxazole; Coupling; Cyclization; ALPHA-KETOHETEROCYCLIC INHIBITORS; BENZOTRIAZOLE RING-CLEAVAGE; HUMAN NEUTROPHIL ELASTASE; IN-VITRO; O-ARYLATION; ANTITUMOR; DESIGN; BENZIMIDAZOLES; CHEMISTRY; PROTOCOL;
D O I
10.1002/slct.201902420
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cu-catalyzed Ullmann coupling was performed for the facile synthesis of diverse benzoxazoles and benzothiazoles in the presence of 1-(hydroxymethyl)-1H-benzotriazole as ligand and K2CO3 as base in anhydrous DMF at 120 degrees C.
引用
收藏
页码:9627 / 9631
页数:5
相关论文
共 52 条
[1]   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
[2]  
Ali M A., 2013, Synthesis, P501
[3]   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
[4]   Synthesis of benzimidazoles and benzoxazoles using TiCl3OTf in ethanol at room temperature [J].
Azizian, Javad ;
Torabi, Parviz ;
Noei, Jalil .
TETRAHEDRON LETTERS, 2016, 57 (02) :185-188
[5]   Synthesis and antimicrobial activity of some new thiazole, thiophene and pyrazole derivatives containing benzothiazole moiety [J].
Bondock, Samir ;
Fadaly, Walid ;
Metwally, Mohamed A. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (09) :3692-3701
[6]   4-THIAZOLIDINONES [J].
BROWN, FC .
CHEMICAL REVIEWS, 1961, 61 (05) :463-521
[7]   Design and synthesis of novel 4-benzothiazole amino quinazolines Dasatinib derivatives as potential anti-tumor agents [J].
Cai, Jin ;
Sun, Min ;
Wu, Xiaoqing ;
Chen, Junqing ;
Wang, Peng ;
Zong, Xi ;
Ji, Min .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 63 :702-712
[8]   PREPARATION OF SOME BENZIMIDAZOLYLAMINO ACIDS - REACTIONS OF AMINO ACIDS WITH O-PHENYLENEDIAMINES [J].
CESCON, LA ;
DAY, AR .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (02) :581-&
[9]   First enantiospecific total synthesis of the antitubercular marine natural product pseudopteroxazole. Revision of assigned stereochemistry [J].
Davidson, JP ;
Corey, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (44) :13486-13489
[10]   Benzoxazole and Benzothiazole Synthesis from Carboxylic Acids in Solution and on Resin by Using Ethyl 2-Cyano-2-(2-nitrobenzenesulfonyloxyimino)acetate and para-Toluenesulfonic Acid [J].
Dev, Dharm ;
Chandra, Jyoti ;
Palakurthy, Nani Babu ;
Thalluri, Kishore ;
Kalita, Tapasi ;
Mandal, Bhubaneswar .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (05) :663-675