Palladium-catalyzed synthesis of isoindoloquinazolinones via dicarbonylation of 1,2-dibromoarenes

被引：26

作者：

Chen, Jianbin ^{[1
]}

Neumann, Helfried ^{[1
]}

Beller, Matthias ^{[1
]}

Wu, Xiao-Feng ^{[1
]}

机构：

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

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 31期

关键词：

CARBONYLATION REACTIONS; AGENT BATRACYLIN; ANALOGS; HETEROCYCLES;

D O I：

10.1039/c4ob01103a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient procedure for the carbonylative synthesis of isoindoloquinazolinones has been developed. Using 1,2-dibromobenzenes and 2-aminobenzyl amine as substrates and palladium as the catalyst, the desired products were isolated in moderate to good yields with the installation of two molecules of carbon monoxide. Notably, this is the first example of carbonylative synthesis of batracylin analogues.

引用

页码：5835 / 5838

页数：4

共 23 条

[1]

Amin A.H., 1970, Prog Drug Res, V14, P218

[2]

[Anonymous], 2012, Bioact. Heterocycl. Compd. Classes Agrochem., DOI [10.1002/9783527664412, DOI 10.1002/9783527664412]

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

Barnard, Christopher F. J. .

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

[4] 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

[5] Multi-component syntheses of heterocycles by transition-metal catalysis [J].

D'Souza, Daniel M. ;

Mueller, Thomas J. J. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1095-1108

[6] Synthesis and cytotoxic activity of conjugates of muramyl and normuramyl dipeptides with batracylin derivatives [J].

Dzierzbicka, K ;

Trzonkowski, P ;

Sewerynek, P ;

Mysliwski, A .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (06) :978-986

[7] Oxidative Carbonylation as a Powerful Tool for the Direct Synthesis of Carbonylated Heterocycles [J].

Gabriele, Bartolo ;

Mancuso, Raffaella ;

Salerno, Giuseppe .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (35) :6825-6839

[8] Synthesis and biological activity of 6H-isoindolo [2,1-a]indol-6-ones, analogues of batracylin, and related compounds [J].

Guillaumel, J ;

Léonce, S ;

Pierré, A ;

Renard, P ;

Pfeiffer, B ;

Arimondo, PB ;

Monneret, C .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (03) :379-386

[9]

GUPTA OP, 1978, INDIAN J EXP BIOL, V16, P1075

[10] Facile approach to diverse range of 1,3-diaza-heterocycles: angular/linear selectivity paradigm and a remarkable intramolecular methyl migration [J].

Kshirsagar, Umesh A. ;

Argade, Narshinha P. .

TETRAHEDRON, 2009, 65 (27) :5244-5250

← 1 2 3 →