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

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-α-amino aldehydes were used for the first time as carbonyl components in a key...

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Published inMolecular diversity Vol. 28; no. 1; pp. 229 - 248
Main Authors Splandesci, Marta, Wróbel, Martyna Z., Madura, Izabela D., Dawidowski, Maciej
Format Journal Article
LanguageEnglish
Published Cham Springer International Publishing 01.02.2024
Springer Nature B.V
Subjects
Amino acids
Biochemistry
Biomedical and Life Sciences
Condensation
Life Sciences
Organic Chemistry
Original
Original Article
Pharmacy
Polymer Sciences
Proteins
Multicomponent reactions
Molecular diversity
Ugi reaction
Ugi 5-center-4-component reaction
2-Oxopiperazines
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Summary: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-α-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-2 H -pyrazino[1,2- a ]pyrazine-3,6,9(4 H )-trione β-turn mimetic and derivatives of 1,6-dioxooctahydropyrrolo[1,2- a ]pyrazine and 3,8-dioxohexahydro-3 H -oxazolo[3,4- a ]pyrazine. Graphical abstract
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ISSN:1381-1991
1573-501X
DOI:10.1007/s11030-023-10760-1