Synthesis of β-mono- and β,γ-di-substituted α-methylene-γ-lactams

[Display omitted] A series of β-mono- and β,γ-di-substituted α-methylene-γ-lactams was synthesized. This method involves the 1,4-addition of nitroalkanes to arylidenemalonates to obtain nitro derivatives using a conventional method and microwave irradiation. Subsequent nitro reduction provided α-car...

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Bibliographic Details
Published in:Tetrahedron letters 2022-09, Vol.107, p.154105, Article 154105
Main Authors: Hernández-Guadarrama, Alexis, Cuevas, Fernando, Montoya-Balbás, Iris J., Román-Bravo, Perla, Linzaga-Elizalde, Irma
Format: Article
Language:English
Subjects:
Arylidenemalonates
Nitroderivatives by microwave irradiation
α-Methylene-γ-lactams
γ-Lactams
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Summary:[Display omitted] A series of β-mono- and β,γ-di-substituted α-methylene-γ-lactams was synthesized. This method involves the 1,4-addition of nitroalkanes to arylidenemalonates to obtain nitro derivatives using a conventional method and microwave irradiation. Subsequent nitro reduction provided α-carbomethoxy-γ-lactam, a versatile molecule that was used to obtain the alcohol. After alcohol, the mesylate was obtained, which was eliminated to give the α-methylene-γ-lactams. The process characteristics are easy work-up, mild reaction conditions, and good yields.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2022.154105