Intramolecular inverse electron-demand [4+2] cycloadditions of ynamidyl-tethered pyrimidines: Comparative studies in trifluorotoluene and sulfolane

被引：3
|
作者：
Donnard, Morgan [1 ,2 ]
Duret, Guillaume [3 ]
Bisseret, Philippe [3 ]
Blanchard, Nicolas [3 ]
机构：
[1] Univ Haute Alsace, Lab Chim Organ & Bioorgan, EA4566, Inst Rech Donnet, 3Bis Rue Alfred Werner, F-68093 Mulhouse, France
[2] Univ Strasbourg, CNRS, UMR 7200, Fac Pharm,Lab Innovat Therapeut, 74 Route Rhin, F-67401 Illkirch Graffenstaden, France
[3] Univ Strasbourg, CNRS, UMR 7509, Lab Chim Mol,ECPM, 25 Rue Becquerel, F-67087 Strasbourg, France
来源：
COMPTES RENDUS CHIMIE | 2017年 / 20卷 / 06期
关键词：
Alkynes; Heterocycles; Nitrogen heterocycles; Cycloaddition; Pericyclic reactions; DIELS-ALDER REACTIONS; TRIFLUOROMETHYLATED ALKYNES; 4-AMINOPYRIDINE DERIVATIVES; ANTIAMNESIC ACTIVITY; AZADIENES; DESIGN; SCOPE;
D O I：
10.1016/j.crci.2017.01.007
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Three representative 6,7-dihydro-5H-cyclopenta[b]pyridin-4-amines were synthesized using an intramolecular inverse electron demand hetero-Diels-Alder/retro-Diels-Alder sequence between pyrimidines (acting as azadienes) and ynamides (acting as dienophiles). Two solvents of this reaction, sulfolane and trifluorotoluene, were compared at 210 degrees C and the former consistently led to higher yields. In addition, these studies confirmed the importance of the steric bulk of the C5-position of the pyrimidinyl cycloaddition precursor. (C) 2017 Academie des sciences. Published by Elsevier Masson SAS.
引用
收藏
页码：643 / 647
页数：5
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