Halopalladation Cyclization of Alkynes with Azides: Selective Synthesis of 4-Haloisoquinolines and 3-Haloindoles

被引：26

作者：

Zhang, Hong-Ping ^{[1
,2
]}

Yu, Shang-Ci ^{[1
]}

Liang, Yun ^{[1
]}

Peng, Peng ^{[1
]}

Tang, Bo-Xiao ^{[1
]}

Li, Jin-Heng ^{[1
]}

机构：

[1] Hunan Normal Univ, Key Lab Chem Biol & Tradit Chinese Med Res, Minist Educ, Changsha 410081, Hunan, Peoples R China

[2] Shaoyang Univ, Dept Biol & Chem Engn, Shaoyang 422000, Peoples R China

来源：

SYNLETT | 2011年 / 07期

基金：

中国国家自然科学基金;

关键词：

palladium; halopalladation; cyclization; 2-alkynyl azide; 4-haloisoquinoline; 3-haloindole; PALLADIUM-CATALYZED IMINOANNULATION; MEDIATED ELECTROPHILIC CYCLIZATION; 2-ALKYNYL BENZYL AZIDES; STEREOSELECTIVE-SYNTHESIS; ISOQUINOLINE ALKALOIDS; SUBSTITUTED ISOQUINOLINES; BETA-PHENYLETHYLAMINES; ASYMMETRIC-SYNTHESIS; TERMINAL ACETYLENES; EFFICIENT SYNTHESIS;

D O I：

10.1055/s-0030-1259722

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new, selective method for the synthesis of 4-haloisoquinolines and 3-haloindoles is presented by the halopalladation cyclizations of alkynes with azides. In the presence of PdX(2) (X = Br, Cl) and halide sources, a variety of 2-alkynyl benzyl azides or 2-alkynyl aryl azides smoothly underwent the halopalladation cyclization reaction to afford the corresponding 3-substituted 4-haloisoquinolines and 2-substituted 3-haloindoles in moderate to good yields.

引用

页码：982 / 988

页数：7

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