Four-component quinazoline synthesis from simple anilines, aromatic aldehydes and ammonium iodide under metal-free conditions

被引：51

作者：

Chen, Jinjin ^{[1
]}

Chang, Dan ^{[1
]}

Xiao, Fuhong ^{[1
]}

Deng, Guo-Jun ^{[1
,2
]}

机构：

[1] Xiangtan Univ, Key Lab Green Organ Synth & Applicat Hunan Prov, Key Lab Environm Friendly Chem & Applicat, Minist Educ,Coll Chem, Xiangtan 411105, Peoples R China

[2] Chinese Acad Sci, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China

来源：

GREEN CHEMISTRY | 2018年 / 20卷 / 24期

基金：

中国国家自然科学基金; 中国博士后科学基金;

关键词：

OXIDATIVE DECARBOXYLATIVE AMINATION; ASYMMETRIC POVAROV REACTION; CATALYZED CASCADE SYNTHESIS; 3-COMPONENT SYNTHESIS; 2-SUBSTITUTED QUINAZOLINES; ENANTIOSELECTIVE SYNTHESIS; ARYLDIAZONIUM SALTS; EFFICIENT SYNTHESIS; SOLVENT-FREE; ANNULATION;

D O I：

10.1039/C8GC02654H

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A four-component procedure for the preparation of substituted quinazolines from anilines, aromatic aldehydes and ammonium iodide is described. The C-H bond ortho to the amino group in anilines was directly functionalized under metal-free conditions. Two aldehydes were involved in this reaction and ammonium iodide was used as one of the nitrogen sources. This reaction provides a strategy for the facile construction of substituted quinazolines from simple anilines and other readily available reactants.

引用

页码：5459 / 5463

页数：5

共 86 条

[1] Chiral Bronsted acid-catalyzed inverse electron-demand aza Diels-Alder reaction [J].

Akiyama, Takahiko ;

Morita, Hisashi ;

Fuchibe, Kohei .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13070-13071

[2] Synthesis, analgesic and anti-inflammatory evaluation of some novel quinazoline derivatives [J].

Alafeefy, Ahmed M. ;

Kadi, Adnan A. ;

Al-Deeb, Omar A. ;

El-Tahir, Kamal E. H. ;

Al-jaber, Nabila A. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (11) :4947-4952

[3] Base-Promoted Synthesis of 2-Aryl Quinazolines from 2-Aminobenzylamines in Water [J].

Chatterjee, Tanmay ;

Kim, Dong In ;

Cho, Eun Jin .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (14) :7423-7430

[4] Assembly of 2-Arylbenzothiazoles through Three-Component Oxidative Annulation under Transition-Metal-Free Conditions [J].

Che, Xingzong ;

Jiang, Jingjing ;

Xiao, Fuhong ;

Huang, Huawen ;

Deng, Guo-Jun .

ORGANIC LETTERS, 2017, 19 (17) :4576-4579

[5] Synthesis of Quinazolines via an Iron-Catalyzed Oxidative Amination of N-H Ketimines [J].

Chen, Cheng-yi ;

He, Fengxian ;

Tang, Guangrong ;

Yuan, Huiqing ;

Li, Ning ;

Wang, Jinmin ;

Faessler, Roger .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (04) :2395-2401

[6] Four-Component Approach to N-Substituted Phenothiazines under Transition-Metal-Free Conditions [J].

Chen, Jinjin ;

Li, Guozheng ;

Xie, Yanjun ;

Liao, Yunfeng ;

Xiao, Fuhong ;

Deng, Guo-Jun .

ORGANIC LETTERS, 2015, 17 (23) :5870-5873

[7] A Novel Ruthenium-Catalyzed Dehydrogenative Synthesis of 2-Arylquinazolines from 2-Aminoaryl Methanols and Benzonitriles [J].

Chen, Mengmeng ;

Zhang, Min ;

Xiong, Biao ;

Tan, Zhenda ;

Lv, Wan ;

Jiang, Huanfeng .

ORGANIC LETTERS, 2014, 16 (22) :6028-6031

[8] Indole-to-Carbazole Strategy for the Synthesis of Substituted Carbazoles under Metal-Free Conditions [J].

Chen, Shanping ;

Li, Yuxia ;

Ni, Penghui ;

Huang, Huawen ;

Deng, Guo-Jun .

ORGANIC LETTERS, 2016, 18 (20) :5384-5387

[9] Unexpected Copper-Catalyzed Cascade Synthesis of Quinazoline Derivatives [J].

Chen, Zhongyan ;

Chen, Jiuxi ;

Liu, Miaochang ;

Ding, Jinchang ;

Gao, Wenxia ;

Huang, Xiaobo ;

Wu, Huayue .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (22) :11342-11348

[10] Chiral Phosphoric Acid-Catalyzed Enantioselective Three-Component Povarov Reaction Using Enecarbamates as Dienophiles: Highly Diastereo- and Enantioselective Synthesis of Substituted 4-Aminotetrahydroquinolines [J].

Dagousset, Guillaume ;

Zhu, Jieping ;

Masson, Geraldine .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (37) :14804-14813

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