Ugi 5-center-4-component reaction of α-amino aldehydes and its application in synthesis of 2-oxopiperazines

被引：1
|
作者：
Splandesci, Marta [1 ]
Wrobel, Martyna Z. [1 ]
Madura, Izabela D. [2 ]
Dawidowski, Maciej [1 ]
机构：
[1] Med Univ Warsaw, Dept Drug Technol & Pharmaceut Biotechnol, Fac Pharm, Banacha 1, PL-02097 Warsaw, Poland
[2] Warsaw Univ Technol, Fac Chem, Noakowskiego 3, PL-00664 Warsaw, Poland
来源：
MOLECULAR DIVERSITY | 2024年 / 28卷 / 01期
关键词：
Multicomponent reactions; Ugi reaction; Ugi 5-center-4-component reaction; 2-Oxopiperazines; Molecular diversity; ACIDS; KETOPIPERAZINES; DERIVATIVES; INHIBITORS; CATALYSIS; 5-CENTER;
D O I：
10.1007/s11030-023-10760-1
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A synthetic route leading to densely functionalized 2-oxopiperazines is presented. The strategy employs a 5-center-4-component variant of Ugi multicomponent reaction followed by a deprotection/cyclization sequence. N-Boc-alpha-amino aldehydes were used for the first time as carbonyl components in a key Ugi 5-center-4-component reaction (U-5C-4CR). It is shown that the presented synthetic route can lead to rigid, heterocyclic scaffolds, as demonstrated by the synthesis of tetrahydro-2H-pyrazino[1,2-a]pyrazine-3,6,9(4H)-trione beta-turn mimetic and derivatives of 1,6-dioxooctahydropyrrolo[1,2-a]pyrazine and 3,8-dioxohexahydro-3H-oxazolo[3,4-a]pyrazine.
引用
收藏
页码：229 / 248
页数：20
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