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

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...

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Bibliographic Details
Published in:Tetrahedron 2004-05, Vol.60 (23), p.5031-5040
Main Authors: Cardillo, Giuliana, Fabbroni, Serena, Gentilucci, Luca, Perciaccante, Rossana, Piccinelli, Fabio, Tolomelli, Alessandra
Format: Article
Language:English
Subjects:
Cycloaddition
Imine
Ketene
Pyridinone
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Summary: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 substituents on the six-membered ring. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.04.021