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.
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页码：803 / 811
页数：9
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