The deprotonative metalation of [1,2,3]triazolo[1,5-a]quinoline. Synthesis of 8-haloquinolin-2-carboxaldehydes

被引：12

作者：

Ballesteros-Garrido, Rafael ^{[1
]}

Leroux, Frederic R. ^{[1
]}

Ballesteros, Rafael ^{[2
]}

Abarca, Belen ^{[2
]}

Colobert, Francoise ^{[1
]}

机构：

[1] Univ Strasbourg, CNRS, Lab Stereochim, ECPM, F-67087 Strasbourg, France

[2] Univ Valencia, Fac Farm, Dept Quim Organ, Valencia 46100, Spain

来源：

TETRAHEDRON | 2009年 / 65卷 / 22期

关键词：

RING-OPENING REACTIONS; ASYMMETRIC CATALYSIS; QUINOLINE DERIVATIVES; DIRECTED LITHIATION; MEDICINAL CHEMISTRY; MAGNESIUM EXCHANGE; PROSTATE-CANCER; TRIAZOLOPYRIDINES; LIGANDS; FUNCTIONALIZATION;

D O I：

10.1016/j.tet.2009.03.058

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New highly functionalized triazoloquinolines were synthesized by applying polar organometallic methods. Double metalation and functionalization provided 3,9-dihalogenated triazoloquinolines. Ring opening of the triazole with loss of nitrogen has been performed for the first time with 3,9-dihalogenated triazoloquinolines allowing the access toward 8-haloquinolin-2-carboxaldehydes under oxidant-free conditions. This approach demonstrates that the triazole ring can be used as protecting group of 2-quinolinecarboxaldehydes, activating the C9-position for lithiation and functionalization by triazole ring opening. 8-Haloquinoline-2-carbaldehydes become in this way readily available. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：4410 / 4417

页数：8

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