Palladium-catalyzed cyclocarbonylation of o-iodoanilines with imidoyl chlorides to produce quinazolin-4(3H)-ones

被引：128

作者：

Zheng, Zhaoyan ^{[1
]}

Alper, Howard ^{[1
]}

机构：

[1] Univ Ottawa, Ctr Catalysis Res & Innovat, Dept Chem, Ottawa, ON K1N 6N5, Canada

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 05期

关键词：

D O I：

10.1021/ol7029454

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A wide variety of substituted quinazolin-4(3H)-ones were prepared in 63-91% yields by the palladium-catalyzed cyclocarbonylation of o-iodoanilines with imidoyl chlorides and carbon monoxide. The reaction is believed to proceed via in situ formation of an amidine, followed by oxidative addition, CO insertion, and intramolecular cyclization to give the substituted quinazolin-4(3H)-ones.

引用

页码：829 / 832

页数：4

共 41 条

[1] A novel method for the synthesis of 4(3H)-quinazolinones [J].

Abdel-Jalil, RJ ;

Voelter, W ;

Saeed, M .

TETRAHEDRON LETTERS, 2004, 45 (17) :3475-3476

[2] TRANSITION-METAL COMPLEX-CATALYZED REDUCTIVE N-HETEROCYCLIZATION - SYNTHESIS OF 4(3H)-QUINAZOLINONE DERIVATIVES FROM N-(2-NITROBENZOYL)AMIDES [J].

AKAZOME, M ;

KONDO, T ;

WATANABE, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) :310-312

[3] PALLADIUM COMPLEX-CATALYZED INTERMOLECULAR REDUCTIVE N-HETEROCYCLIZATION - NOVEL SYNTHESIS OF QUINAZOLINE DERIVATIVES FROM 2-NITROBENZALDEHYDE OR 2-NITROPHENYL KETONES WITH FORMAMIDE [J].

AKAZOME, M ;

YAMAMOTO, J ;

KONDO, T ;

WATANABE, Y .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 494 (1-2) :229-233

[4]

BOGENTOFT C, 1969, ACTA PHARM SUEC, V6, P485

[5]

Bogert M.T., 1902, J AM CHEM SOC, V24, P1031, DOI [10.1021/ja02025a001, DOI 10.1021/JA02025A001]

[6] 3,5-Bibrom-2-aminobenzoic acid - Its nitrile and the synthesis of quinazolines form the latter [J].

Bogert, MT ;

Hand, WF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1903, 25 (09) :935-947

[7] Solid-phase synthesis of 1,3-dialkyl quinazoline-2,4-diones [J].

Buckman, BO ;

Mohan, R .

TETRAHEDRON LETTERS, 1996, 37 (26) :4439-4442

[8] Synthesis and in vitro antitumor activity of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains [J].

Cao, SL ;

Feng, YP ;

Jiang, YY ;

Liu, SY ;

Ding, GY ;

Li, RT .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (07) :1915-1917

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

Connolly, DJ ;

Cusack, D ;

O'Sullivan, TP ;

Guiry, PJ .

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

[10] Quinazoline alkaloids in nature [J].

D'yakonov A.L. ;

Telezhenetskaya M.V. .

Chemistry of Natural Compounds, 1997, 33 (3) :221-267

← 1 2 3 4 5 →