Unusual peptidomimetic reaction of 1,2-diaza-1,3-butadienes: Straightforward entry to 2,3,6-triazabicyclo[3.2.1]oct-3-enes, 5-oxo-4,5-dihydro-2-pyrazines, and 2-carbonyl-2-oxopropylaminoacetates

被引：9
作者：
Attanasi, Orazio A.
De Crescentini, Lucia
Filippone, Paolino
Giorgi, Gianluca
Mantellini, Fabio
Mazzanti, Andrea
机构：
[1] Univ Urbino Carlo Bo, Inst Chim Organ, Fac Sci Matemat Fisiche & Nat, I-61029 Urbino, Italy
[2] Univ Siena, Dipartimento Chim, I-53100 Siena, Italy
[3] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy
来源：
SYNLETT | 2006年 / 15期
关键词：
Michael additions; amino acids; 1,2-diaza-1,3-butadienes; triazabicyclo derivatives; pyrazines;
D O I：
10.1055/s-2006-950409
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The peptido-mimetic reaction between 4-dialkylaminocarbonyl-1,2-diaza-1,3-butadienes and sarcosine ethyl ester gave alpha-aminohydrazones. These compounds, in ethanol under reflux with sodium hydride, furnished new and unexpected 7-oxo-8-oxa-2,3,6-triazabicyclo[3.2.1]oct-3-ene-2-carboxylates and 5-oxo-4,5-dihydro-2-pyrazines. By treatment with Amberlyst 15H in acetone-water (10:1), the same hydrazones were converted into the corresponding ethyl 2-[{1-[(diethylamino)carbonyl]-2-oxopropyl} (methyl)am ino]acetates.
引用
收藏
页码：2403 / 2406
页数：4
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