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

被引：3

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

页码：3298 / 3306

页数：9

共 26 条

[1] Ruthenium-Catalyzed C-H/N-O Bond Functionalization: Green Isoquinolone Syntheses in Water
Ackermann, Lutz
Fenner, Sabine
[J]. ORGANIC LETTERS, 2011, 13 (24) : 6548 - 6551
[2] Ruthenium-Catalyzed Oxidative Annulation by Cleavage of C-H/N-H Bonds
Ackermann, Lutz
Lygin, Alexander V.
Hofmann, Nora
[J]. 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
Alagarsamy, Veerachamy
Pathak, Urvishbhai S.
[J]. 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
Cheng, Ran
Guo, Tianjian
Zhang-Negrerie, Daisy
Du, Yunfei
Zhao, Kang
[J]. SYNTHESIS-STUTTGART, 2013, 45 (21): : 2998 - 3006
[5] Copper-Catalyzed Synthesis of 2-Arylquinazolinones from 2-Arylindoles with Amines or Ammoniums
Feng, Yadong
Li, Yudong
Cheng, Guolin
Wang, Lianhui
Cui, Xiuling
[J]. 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
Grover, G
Kini, SG
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (02) : 256 - 262
[7] Metal-Catalyzed Annulations through Activation and Cleavage of C-H Bonds
Gulias, Moises
Luis Mascarenas, Jose
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (37) : 11000 - 11019
[8] Selectivity Control in Ruthenium(II)-Catalyzed C-H/N-O Activation with Alkynyl Bromides
Huang, Huawen
Nakanowatari, Sachiyo
Ackermann, Lutz
[J]. 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
Hyster, Todd K.
Dalton, Derek M.
Rovis, Tomislav
[J]. 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
Hyster, Todd K.
Ruhl, Kyle E.
Rovis, Tomislav
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) : 5364 - 5367

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