Chemoselective synthesis of 6-amino(alkoxy)-1,4,5,6-tetrahydropyridines from cyclic β-alkoxyvinyl α-ketoester

[Display omitted] •Cyclic enones are efficient building blocks for the synthesis of tetrahydropyridines.•Chemoselective synthesis of tetrahydropyridines from cyclic β-alkoxyvinyl α-ketoester.•Cyclic enones α-ketoester provides chemoselective synthesis of tetrahydropyridines. The synthetic versatilit...

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Bibliographic Details
Published in:Tetrahedron letters 2019-12, Vol.60 (52), p.151336, Article 151336
Main Authors: Pretto, Leida M., Mittersteiner, Mateus, Andrade, Valquiria P., Bonacorso, Helio G., Martins, Marcos A.P., Zanatta, Nilo
Format: Article
Language:English
Subjects:
ANRORC
Pyran
Tetrahydropyridines
α-Ketoesters
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Summary:[Display omitted] •Cyclic enones are efficient building blocks for the synthesis of tetrahydropyridines.•Chemoselective synthesis of tetrahydropyridines from cyclic β-alkoxyvinyl α-ketoester.•Cyclic enones α-ketoester provides chemoselective synthesis of tetrahydropyridines. The synthetic versatility of ethyl 2-(2-ethoxy-3,4-dihydro-2H-pyran-5-yl)-2-oxoacetate for the synthesis of ethyl 2-oxo-2-(1-alkyl/aryl-6-(amino/ethoxy)-1,4,5,6-tetrahydropyridin-3-yl)acetates, from the reaction with primary amines, is presented. The methodology proposed herein is highly chemoselective, and twenty products were obtained in moderate to good yields (up to 87%).
ISSN:0040-4039
DOI:10.1016/j.tetlet.2019.151336