Base-Controlled Selectivity in the Synthesis of Linear and Angular Fused Quinazolinones by a Palladium-Catalyzed Carbonylation/Nucleophilic Aromatic Substitution Sequence

被引：119

作者：

Chen, Jianbin ^{[1
]}

Natte, Kishore ^{[1
]}

Spannenberg, Anke ^{[1
]}

Neumann, Helfried ^{[1
]}

Langer, Peter ^{[1
]}

Beller, Matthias ^{[1
]}

Wu, Xiao-Feng ^{[1
]}

机构：

[1] Univ Rostock eV, Leibniz Inst Katalyse, D-18059 Rostock, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 29期

关键词：

carbonylation; domino reactions; nucleophilic aromatic substitution; palladium catalysts; quinazolinones; ONE-POT SYNTHESIS; ULLMANN CONDENSATION; DOMINO REACTIONS; HETEROCYCLES; RUTAECARPINE; DERIVATIVES; 4(3H)-QUINAZOLINONES; PYRIDOQUINAZOLONES; CYCLOADDITION; NUCLEOPHILES;

D O I：

10.1002/anie.201402779

中图分类号：

O6 [化学];

学科分类号：

070301 [无机化学];

摘要：

A new approach for the facile synthesis of fused quinazolinone scaffolds through a palladium-catalyzed carbonylative coupling followed by an intramolecular nucleophilic aromatic substitution is described. The base serves as the key modulator: Whereas DBU gives rise to the linear isomers, Et3N promotes the preferential formation of angular products. Interestingly, a light-induced 4+4 reaction of the product was also observed.

引用

页码：7579 / 7583

页数：5

共 50 条

[1]

[Anonymous], 2011, ANGEW CHEM

[2]

Arora D., 2011, PHARMACOLOGYONLINE, V3, P659

[3]

Light-Induced Hetero-Diels-Alder Cycloaddition: A Facile and Selective Photoclick Reaction [J].

Arumugam, Selvanathan ;

Popik, Vladimir V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (14) :5573-5579

[4]

Palladium-Catalyzed Carbonylation-A Reaction Come of Age [J].

Barnard, Christopher F. J. .

ORGANOMETALLICS, 2008, 27 (21) :5402-5422

[5]

New azole antifungals.: 3.: Synthesis and antifungal activity of 3-substituted-4(3H)-quinazolinones [J].

Bartroli, J ;

Turmo, E ;

Algueró, M ;

Boncompte, E ;

Vericat, ML ;

Conte, L ;

Ramis, J ;

Merlos, M ;

García-Rafanell, J ;

Forn, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (11) :1869-1882

[6]

Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds [J].

Brennfuehrer, Anne ;

Neumann, Helfried ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4114-4133

[7]

Brennfuhrer A., 2009, ANGEW CHEM, V121, P4176, DOI 10.1002/ange.200900013

[8]

Chawla A., 2013, INT RES J PHARM, V4, P49, DOI DOI 10.7897/2230-8407.04309

[9]

Efficient Copper-Catalyzed Synthesis of Fused Pyridoquinazolones [J].

Chen, Lujun ;

Fu, Hua ;

Qiao, Renzhong .

SYNLETT, 2011, (13) :1930-1936

[10]

Synthesis of quinazolinones and quinazolines [J].

Connolly, DJ ;

Cusack, D ;

O'Sullivan, TP ;

Guiry, PJ .

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

← 1 2 3 4 5 →