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.
Practical synthesis of 3-bromo-5,6-dihydropyridin-2-ones via β,γ-unsaturated α-bromo-ketene/imine cycloaddition / CARDILLO G.; FABBRONI S.; GENTILUCCI L.; PERCIACCANTE R.; PICCINELLI F.; TOLOMELLI A.. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 60:23(2004), pp. 5031-5040. [10.1016/j.tet.2004.04.021]
Practical synthesis of 3-bromo-5,6-dihydropyridin-2-ones via β,γ-unsaturated α-bromo-ketene/imine cycloaddition
CARDILLO, GIULIANA;FABBRONI, SERENA;GENTILUCCI, LUCA;PERCIACCANTE, ROSSANA;PICCINELLI, FABIO;TOLOMELLI, ALESSANDRA
2004
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 substituents on the six-membered ring.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
