A Simple and Efficient Approach to Quinazolinones under Mild Copper-Catalyzed Conditions

被引：298

作者：

Liu, Xiaowei ^{[1
]}

Fu, Hua ^{[1
]}

Jiang, Yuyang ^{[1
,2
]}

Zhao, Yufen ^{[1
]}

机构：

[1] Tsinghua Univ, Dept Chem, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Minist Educ, Beijing 100084, Peoples R China

[2] Tsinghua Univ, Key Lab Chem Biol Guangdong Prov, Grad Sch, Shenzhen 518057, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 02期

基金：

中国国家自然科学基金;

关键词：

copper; cyclization; guanidines; heterocycles; quinazolinone; COUPLING REACTIONS; NITROGEN-HETEROCYCLES; ROOM-TEMPERATURE; ULLMANN; ALKALOIDS; CHEMISTRY; SUBSTITUTION; CHLORIDE; ETHERS;

D O I：

10.1002/anie.200804675

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Cop some rings: A simple and highly efficient copper-catalyzed method for the synthesis of quinazolinone derivatives through the reaction of substituted 2-halobenzoic acids with amidines or guanidines under mild conditions has been developed (see scheme). The method has economical and practical advantages. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：348 / 351

页数：4

共 35 条

[1]

[Anonymous], 2007, ANGEW CHEM

[2]

[Anonymous], 2006, Angew. Chem, DOI DOI 10.1002/ANGE.200602917

[3] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[4] Rapid access to oxindoles by the combined use of an Ugi four-component reaction and a microwave-assisted intramolecular Buchwald-Hartwig amidation reaction [J].

Bonnaterre, Florence ;

Bois-Choussy, Michele ;

Zhu, Jieping .

ORGANIC LETTERS, 2006, 8 (19) :4351-4354

[5] Mild Ullmann-type biaryl ether formation reaction by combination of ortho-substituent and ligand effects [J].

Cai, Q ;

Zou, BL ;

Ma, DW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (08) :1276-1279

[6]

Cai Q., 2006, Angewandte Chemie, V118, P1298

[7] Synthesis of quinazolinones and quinazolines [J].

Connolly, DJ ;

Cusack, D ;

O'Sullivan, TP ;

Guiry, PJ .

TETRAHEDRON, 2005, 61 (43) :10153-10202

[8]

Deng Y., 2000, J. Chin. Pharm. Sci., V9, P116

[9] Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis [J].

Evano, Gwilherm ;

Blanchard, Nicolas ;

Toumi, Mathieu .

CHEMICAL REVIEWS, 2008, 108 (08) :3054-3131

[10] The preparation and resolution of 2-(2-pyridyl)- and 2-(2-pyrazinyl)-Quinazolinap and their application in palladium-catalysed allylic substitution [J].

Flanagan, SP ;

Goddard, R ;

Guiry, PJ .

TETRAHEDRON, 2005, 61 (41) :9808-9821

← 1 2 3 4 →