Chemoselective synthesis of 6-amino(alkoxy)-1, 4, 5, 6-tetrahydropyridines from cyclic β-alkoxyvinyl α-ketoester. Issue 52 (26th December 2019)

• Record Type: Journal Article
• Authors: Pretto, Leida M.; Mittersteiner, Mateus; Andrade, Valquiria P.; Bonacorso, Helio G.; Martins, Marcos A.P.; Zanatta, Nilo
• Is Part Of: Tetrahedron letters. Volume 60:Issue 52(2019)
• Publication Date: 2019-12-26
• Subjects: Tetrahydropyridines -- Pyran -- α-Ketoesters -- ANRORC; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.151336
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: 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. Abstract: The synthetic versatility of ethyl 2-(2-ethoxy-3, 4-dihydro-2 H -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%).