Rhodium(III)-Catalyzed Synthesis of Quinazolin-4(3H)-ones with N-Methoxyamides as Synthesis Reagents

被引:4
作者
Zhou, Guanyu [1 ]
Huang, Zhibin [1 ]
Xu, Xu [1 ]
Fang, Zhang [1 ]
Huang, Pengcheng [1 ]
Deng, Zefeng [1 ]
Li, Bao [2 ]
Zhao, Yingsheng [1 ,2 ]
机构
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
[2] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453000, Henan, Peoples R China
来源
SYNTHESIS-STUTTGART | 2022年 / 54卷 / 14期
关键词
rhodium; quinazolin-4(3H)-one; C-H activation; cyclization; N-methoxyamide; ONE-POT SYNTHESIS; ACTIVATION; ANNULATION; ACID; QUINAZOLINONES; BENZAMIDES; CLEAVAGE;
D O I
10.1055/a-1792-9930
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical method to synthesize quinoxalinones via intra/intermolecular amination using rhodium as the catalyst was developed. A wide variety of quinoxalinones were prepared from N-methoxybenzamides in moderate to excellent yields. Gram-scale reactions were also achieved, highlighting the synthetic importance of this new transformation.
引用
收藏
页码:3298 / 3306
页数:9
相关论文
共 26 条
[1]   Ruthenium-Catalyzed C-H/N-O Bond Functionalization: Green Isoquinolone Syntheses in Water [J].
Ackermann, Lutz ;
Fenner, Sabine .
ORGANIC LETTERS, 2011, 13 (24) :6548-6551
[2]   Ruthenium-Catalyzed Oxidative Annulation by Cleavage of C-H/N-H Bonds [J].
Ackermann, Lutz ;
Lygin, Alexander V. ;
Hofmann, Nora .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (28) :6379-6382
[3]   Synthesis and antihypertensive activity of novel 3-benzyl-2-substituted-3H-[1,2,4]triazolo[5,1-b]quinazolin-9-ones [J].
Alagarsamy, Veerachamy ;
Pathak, Urvishbhai S. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (10) :3457-3462
[4]   One-Pot Synthesis of Quinazolinones from Anthranilamides and Aldehydes via p-Toluenesulfonic Acid Catalyzed Cyclocondensation and Phenyliodine Diacetate Mediated Oxidative Dehydrogenation [J].
Cheng, Ran ;
Guo, Tianjian ;
Zhang-Negrerie, Daisy ;
Du, Yunfei ;
Zhao, Kang .
SYNTHESIS-STUTTGART, 2013, 45 (21) :2998-3006
[5]   Copper-Catalyzed Synthesis of 2-Arylquinazolinones from 2-Arylindoles with Amines or Ammoniums [J].
Feng, Yadong ;
Li, Yudong ;
Cheng, Guolin ;
Wang, Lianhui ;
Cui, Xiuling .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (14) :7099-7107
[6]   Synthesis and evaluation of new quinazolone derivatives of nalidixic acid as potential antibacterial and antifungal agents [J].
Grover, G ;
Kini, SG .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (02) :256-262
[7]   Metal-Catalyzed Annulations through Activation and Cleavage of C-H Bonds [J].
Gulias, Moises ;
Luis Mascarenas, Jose .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (37) :11000-11019
[8]   Selectivity Control in Ruthenium(II)-Catalyzed C-H/N-O Activation with Alkynyl Bromides [J].
Huang, Huawen ;
Nakanowatari, Sachiyo ;
Ackermann, Lutz .
ORGANIC LETTERS, 2017, 19 (17) :4620-4623
[9]   Ligand design for Rh(III)-catalyzed C-H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones [J].
Hyster, Todd K. ;
Dalton, Derek M. ;
Rovis, Tomislav .
CHEMICAL SCIENCE, 2015, 6 (01) :254-258
[10]   A Coupling of Benzamides and Donor/Acceptor Diazo Compounds To Form γ-Lactams via Rh(III)-Catalyzed C-H Activation [J].
Hyster, Todd K. ;
Ruhl, Kyle E. ;
Rovis, Tomislav .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) :5364-5367