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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Bibliographic Details
Published in:Molecular diversity 2024-02, Vol.28 (1), p.229-248
Main Authors: Splandesci, Marta, Wróbel, Martyna Z., Madura, Izabela D., Dawidowski, Maciej
Format: Article
Language:English
Subjects:
Amino acids
Biochemistry
Biomedical and Life Sciences
Condensation
Life Sciences
Organic Chemistry
Original
Original Article
Pharmacy
Polymer Sciences
Proteins
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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
ISSN:1381-1991
1573-501X
DOI:10.1007/s11030-023-10760-1