Synthesis of Tetrahydropyridazine Amino Acid Derivatives by a Formal [4+2] Cycloaddition Reaction of 1,2-Diaza-1,3-dienes with Dehydroalanine Esters

被引：5

作者：

Attanasi, Orazio A. ^{[1
]}

Favi, Gianfranco ^{[1
]}

Giorgi, Gianluca ^{[2
]}

Mantellini, Fabio ^{[1
]}

Moscatelli, Giada ^{[1
]}

Piersanti, Giovanni ^{[3
]}

机构：

[1] Univ Urbino Carlo Bo, Dipartimento Sci Terra Vita & Ambiente DiSTeVA, I-61029 Urbino, PU, Italy

[2] Univ Siena, Dipartimento Chim, I-53100 Siena, Italy

[3] Univ Urbino Carlo Bo, Dipartimento Sci Biomol, I-61029 Urbino, PU, Italy

来源：

CURRENT ORGANIC SYNTHESIS | 2013年 / 10卷 / 05期

关键词：

Cycloaddition reaction; dehydroalanine esters; 1,2-Diaza-1,3-dienes; N; N-disubstituted quaternary center; nitrogen heterocycles; tetrahydropyridazine amino acids; STEREOSELECTIVE-SYNTHESIS; DIASTEREOSELECTIVE CYCLOPROPANATION; RECEPTOR; ANALOGS; CONSTRUCTION; INHIBITORS; ALKYLATION; ANNULATION; AZOALKENES; DIVERGENT;

D O I：

10.2174/1570179411310050011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient formal inverse electron demand aza Diels-Alder reaction of 1,2-diaza-1,3-dienes (DDs) is accomplished using dehydroalanine esters (DhAs) as electron-rich dienophiles. Both diastereoisomers of unprecedented alpha,alpha-disubstituted cyclic tetrahydropyridazine amino acids were obtained in excellent yields, in refluxing acetonitrile without activation.

引用

页码：803 / 811

页数：9

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