Rhodium-Catalyzed Merging of 2-Arylquinazolinone and 2,2-Difluorovinyl Tosylate: Diverse Synthesis of Monofluoroolefin Quinazolinone Derivatives

被引:14
作者
Wang, Ning [1 ]
Yang, Qin [1 ]
Deng, Zhihong [1 ]
Mao, Xuechun [1 ]
Peng, Yiyuan [1 ]
机构
[1] Jiangxi Normal Univ, Key Lab Funct Small Organ Mol, Jiangxi Prov Key Lab Green Chem, Minist Educ, Nanchang 330022, Jiangxi, Peoples R China
基金
中国国家自然科学基金;
关键词
FLUORINATED ALCOHOLS; H FLUOROALKENYLATION; INHIBITORS; FUNCTIONALIZATION; PHARMACEUTICALS; HETEROARENES; ALKALOIDS; CHEMISTRY; QUINOLINE; MIMICS;
D O I
10.1021/acsomega.0c01344
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient method for the synthesis of 2-(o-monofluoroalkenylaryl)quinazolinone derivatives was developed. In this context, the quinazolinone ring served as the inherent directing group, 2,2-difluorovinyl tosylate was used as the monofluoroolefin synthon, and Rh(III)-catalyzed C-H bond difluorovinylation of 2-arylquinazolinons was performed to give the corresponding monofluoroalkene-containing quinazolinons in yields of 65-92%. The method is characterized by broad synthetic utility, mild conditions, and high efficiency.
引用
收藏
页码:14635 / 14644
页数:10
相关论文
共 95 条
[61]  
Taguchi T.Y., 2009, Fluorine in Medicinal Chemistry and Chemical Biology, P257, DOI DOI 10.1002/9781444312096.CH10
[62]   Copper-Catalyzed Stereoselective Defluorinative Borylation and Silylation of gem-Difluoroalkenes [J].
Tan, Dong-Hang ;
Lin, E. ;
Ji, Wei-Wei ;
Zeng, Yao-Fu ;
Fan, Wen-Xin ;
Li, Qingjiang ;
Gao, Hui ;
Wang, Honggen .
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (05) :1032-1037
[63]   Palladium-Catalyzed Defluorinative Coupling of 1-Aryl-2,2-Difluoroalkenes and Boronic Acids: Stereoselective Synthesis of Monofluorostilbenes [J].
Thornbury, Richard T. ;
Toste, F. Dean .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (38) :11629-11632
[64]   Direct α-Monofluoroalkenylation of Heteroatomic Alkanes via a Combination of Photoredox Catalysis and Hydrogen-Atom-Transfer Catalysis [J].
Tian, Hao ;
Xia, Qing ;
Wang, Qiang ;
Dong, Jianyang ;
Liu, Yuxiu ;
Wang, Qingmin .
ORGANIC LETTERS, 2019, 21 (12) :4585-4589
[65]   Rh(iii)-Catalyzed -fluoroalkenylation of N-nitrosoanilines with 2,2-difluorovinyl tosylates via C-H bond activation [J].
Tian, Miaomiao ;
Yang, Xifa ;
Zhang, Bo ;
Liu, Bingxian ;
Li, Xingwei .
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (23) :3406-3409
[66]   F- Nucleophilic-Addition-Induced Allylic Alkylation [J].
Tian, Panpan ;
Wang, Cheng-Qiang ;
Cai, Sai-Hu ;
Song, Shengjin ;
Ye, Lu ;
Feng, Chao ;
Loh, Teck-Peng .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (49) :15869-15872
[67]   Rhodium-catalysed C(sp2)-C(sp2) bond formation via C-H/C-F activation [J].
Tian, Panpan ;
Feng, Chao ;
Loh, Teck-Peng .
NATURE COMMUNICATIONS, 2015, 6
[68]   Fluoro-olefins as peptidomimetic inhibitors of dipeptidyl peptidases [J].
Van der Veken, P ;
Senten, K ;
Kertèsz, I ;
De Meester, I ;
Lambeir, AM ;
Maes, MB ;
Scharpé, S ;
Haemers, A ;
Augustyns, K .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (06) :1768-1780
[69]   Synthesis of terminal monofluoro olefins [J].
van Steenis, JH ;
van der Gen, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (19) :2117-2133
[70]   Ruthenium-Catalyzed Regioselective Alkenylation/Tandem Hydroamidative Cyclization of Unmasked Quinazolinones Using Terminal Alkynes [J].
Viveki, Amol B. ;
Mhaske, Santosh B. .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (16) :8906-8913