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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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
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Language:English
Subjects:
Arylidenemalonates
Nitroderivatives by microwave irradiation
α-Methylene-γ-lactams
γ-Lactams
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cited_by cdi_FETCH-LOGICAL-c221t-c3106af3d47a7aa7f908e9a753aba78690162cafbc079202971deae4765c7bbf3
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container_start_page 154105
container_title Tetrahedron letters
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creator Hernández-Guadarrama, Alexis
Cuevas, Fernando
Montoya-Balbás, Iris J.
Román-Bravo, Perla
Linzaga-Elizalde, Irma
description [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.
doi_str_mv 10.1016/j.tetlet.2022.154105
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subjects Arylidenemalonates
Nitroderivatives by microwave irradiation
α-Methylene-γ-lactams
γ-Lactams
title Synthesis of β-mono- and β,γ-di-substituted α-methylene-γ-lactams
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