Tetrahedron

Practical synthesis of 3-bromo-5, 6-dihydropyridin-2-ones via β, γ-unsaturated α-bromo-ketene/imine cycloaddition

…, S Fabbroni, L Gentilucci, R Perciaccante, F Piccinelli…

Index: Cardillo, Giuliana; Fabbroni, Serena; Gentilucci, Luca; Perciaccante, Rossana; Piccinelli, Fabio; Tolomelli, Alessandra Tetrahedron, 2004 , vol. 60, # 23 p. 5031 - 5040

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Citation Number: 16

Abstract

An approach to 3-bromo-4-alkyl-6-aryl-5, 6-dihydropyridin-2-ones and 3-bromo-5-ethyl-6- aryl-5, 6-dihydropyridin-2-ones starting from β, γ-unsaturated α-bromoketenes and imines is reported. The presence of a bromine atom on the double bond allows performing aziridination or bromine displacement with an amine. The reaction gave fused bicyclic N- allyl-aziridines or 3-amino-substituted 5, 6-dihydropyridin-2-ones, depending on the ...