One-Pot Synthesis of 1,2-Disubstituted 4-, 5-, 6-, and 7-Azaindoles from Amino-o-halopyridines via N-Arylation/Sonogashira/Cyclization Reaction

被引：15

作者：

Purificacao, Sara I. ^{[1
]}

Pires, Marina J. D. ^{[1
]}

Rippel, Rafael ^{[1
]}

Sofia Santos, A. ^{[1
]}

Marques, M. Manuel B. ^{[1
]}

机构：

[1] Univ Nova Lisboa, LAQV REQUIMTE, Dept Quim, Fac Ciencias & Tecnol, Campus Caparica, P-2829516 Caparica, Portugal

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 19期

关键词：

CATALYZED AMINATION; AMINOPYRIDINES; 5-AZAINDOLES; INHIBITORS; ALKALOIDS; ARYLATION;

D O I：

10.1021/acs.orglett.7b02403

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct synthesis of several 1,2-disubstituted 4-, 5-, 6-, and 7-azaindoles from available amino-o-halopyridines is described. This procedure involves a palladium -catalyzed N-arylation followed by a Sonogashira reaction and subsequent cyclization in a one-pot manner, exhibiting a wide scope and compatibility with electron-withdrawing and electron-donating groups. The strategy represents an advancement in azaindole chemistry with a straightforward approach toward 1,2-disubstituted azaindoles, while avoiding complex N-arylations of hindered 2-substituted azaindoles and difficult purification steps of intermediates.

引用

页码：5118 / 5121

页数：4

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