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

页码：643 / 647

页数：5

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