Microwave-Assisted [3+2] Cycloaddition and Suzuki-Miyaura Cross-Coupling for a Concise Access to Polyaromatic Scaffolds

被引：15

作者：

Hedou, Damien ^{[1
,2
,3
,4
,5
]}

Deau, Emmanuel ^{[1
,2
,3
,4
,5
]}

Dubouilh-Benard, Carole ^{[1
,2
,3
,4
,5
]}

Sanselme, Morgane ^{[6
]}

Martinet, Anthony ^{[7
]}

Chosson, Elizabeth ^{[1
,2
,3
,4
,5
]}

Levacher, Vincent ^{[1
,2
,3
,4
,5
]}

Besson, Thierry ^{[1
,2
,3
,4
,5
]}

机构：

[1] Univ Rouen, UMR 6014, COBRA, Normandie Univ, F-76821 Mont St Aignan, France

[2] Univ Rouen, FR 3038, F-76821 Mont St Aignan, France

[3] INSA Rouen, F-76821 Mont St Aignan, France

[4] CNRS, F-76821 Mont St Aignan, France

[5] IRCOF, F-76821 Mont St Aignan, France

[6] IRCOF, Unite Cristallogenese, Lab SMS, F-76821 Mont St Aignan, France

[7] Anton Paar France SAS, F-91967 Courtaboeuf, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 33期

关键词：

Nitrogen heterocycles; Cycloaddition; Cross-coupling; Microwave chemistry; Polyaromatics; ONE-POT SYNTHESIS; BIOLOGICAL EVALUATION; 1,2,3-TRIAZOLES; INHIBITORS; ANALOGS; AZIDES;

D O I：

10.1002/ejoc.201301014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel 3-(prop-2-ynyl)pyrido[2,3-d]pyrimidin-4(3H)-ones and 3-(prop-2-ynyl)quinazolin-4(3H)-ones have been synthesized in a high-yielding microwave-assisted one-pot procedure. The one-pot sequence was conveniently extended to the synthesis of commercially unavailable 6-bromo-N-3-propargylpyrido[2,3-d]pyrimidinone by a regiocontrolled bromination with NBS. The synthetic scaffolds were successfully converted into triazoles by copper(I)-catalyzed [3+2] cycloaddition and substituted at the 6-position by Suzuki-Miyaura cross-coupling in high overall yields.

引用

页码：7533 / 7545

页数：13

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