Rhodium-Catalyzed C-H Activation of 2-Arylquinazolinones and Cyclization with Elemental Sulfur via C-S/S-N Bond Formation to Access 7 H -Benzo[4,5]isothiazolo[3,2-b ]quinazolinones

被引:1
作者
Zhang, Xinqin [1 ]
Wu, Qiong [1 ]
Yang, Qin [1 ]
Fu, Yang [1 ]
Peng, Yiyuan [1 ]
机构
[1] Jiangxi Normal Univ, Key Lab Green Chem Jiangxi Prov, 99 Ziyang Ave, Nanchang 330022, Peoples R China
来源
SYNTHESIS-STUTTGART | 2023年 / 55卷 / 20期
基金
中国国家自然科学基金;
关键词
C-H activation; quinazoline; heterocycle; sulfur; benzisothiazoloquinazolinone; NATURALLY-OCCURRING QUINAZOLINONE; QUINOLINE; CHEMISTRY;
D O I
10.1055/a-2147-2620
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient method for the synthesis of 7H-benzo[4,5] isothiazolo[3,2-b]quinazolin-7-ones by the reaction of 2-arylquinazolin-4(3H)-ones and elemental sulfur is described. The rhodium-catalyzed C-H activation of 2-arylquinazolinones and cyclization with elemental sulfur via one-step formation of C-S/N-S bonds to give the corresponding 7H-benzo[4,5] isothiazolo[3,2-b]quinazolinones is realized in good to high yields with good functional group tolerance.
引用
收藏
页码:3364 / 3372
页数:9
相关论文
共 51 条
[1]   Development of certain novel N-(2-(2-(2-oxoindolin-3-ylidene)hydrazinecarbonyl)phenyl)-benzamides and 3-(2-oxoindolin-3-ylideneamino)-2-substituted quinazolin-4(3H)-ones as CFM-1 analogs: Design, synthesis, QSAR analysis and anticancer activity [J].
Alafeefy, Ahmed M. ;
Ashour, Abdelkader E. ;
Prasad, Onkar ;
Sinha, Leena ;
Pathak, Shilendra ;
Alasmari, Fatimah A. ;
Rishi, Arun K. ;
Abdel-Aziz, Hatem A. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 92 :191-201
[2]   Recent advances in the pharmacological diversification of quinazoline/quinazolinone hybrids [J].
Auti, Prashant S. ;
George, Ginson ;
Paul, Atish T. .
RSC ADVANCES, 2020, 10 (68) :41353-41392
[3]   An efficient copper mediated synthetic methodology for benzo[d]isothiazol-3(2H)-ones and related sulfur-nitrogen heterocycles [J].
Bhakuni, Bhagat Singh ;
Balkrishna, Shah Jaimin ;
Kumar, Amit ;
Kumar, Sangit .
TETRAHEDRON LETTERS, 2012, 53 (11) :1354-1357
[4]   2-(4-aminophenyl)benzothiazoles: novel agents with selective profiles of in vitro anti-tumour activity [J].
Bradshaw, TD ;
Wrigley, S ;
Shi, DF ;
Schultz, RJ ;
Paull, KD ;
Stevens, MFG .
BRITISH JOURNAL OF CANCER, 1998, 77 (05) :745-752
[5]   Cu(II)-Mediated C-S/N-S Bond Formation via C-H Activation: Access to Benzoisothiazolones Using Elemental Sulfur [J].
Chen, Fa-Jie ;
Liao, Gang ;
Li, Xin ;
Wu, Jun ;
Shi, Bing-Feng .
ORGANIC LETTERS, 2014, 16 (21) :5644-5647
[6]   THE CHEMISTRY OF SULFENAMIDES [J].
CRAINE, L ;
RABAN, M .
CHEMICAL REVIEWS, 1989, 89 (04) :689-712
[7]   Occupational contact dermatitis caused by N-butyl-1,2-benzisothiazolin-3-one in a cutting fluid [J].
Dahlin, Jakob ;
Isaksson, Marlene .
CONTACT DERMATITIS, 2015, 73 (01) :60-U86
[8]  
Fontana G., 2010, Curr. Bioact. Compd, V6, P284, DOI DOI 10.2174/157340710793237290
[9]   Ziprasidone in the treatment of bipolar disorder with comorbid obsessive-compulsive disorder and gambling disorder [J].
Gan, Zhaoyu ;
Zhang, Ming ;
Han, Hongying ;
Zhu, Qi ;
Li, Kanglai .
BIPOLAR DISORDERS, 2020, 22 (04) :425-428
[10]   4(3H)-Quinazolinone derivatives: Promising antibacterial drug leads [J].
Gatadi, Srikanth ;
Lakshmi, T. Vasanta ;
Nanduri, Srinivas .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2019, 170 :157-172