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

被引：15
作者：
Cardillo, G [1 ]
Fabbroni, S [1 ]
Gentilucci, L [1 ]
Perciaccante, R [1 ]
Piccinelli, F [1 ]
Tolomelli, A [1 ]
机构：
[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
来源：
TETRAHEDRON | 2004年 / 60卷 / 23期
关键词：
D O I：
10.1016/j.tet.2004.04.021
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 beta,gamma-unsaturated alpha-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. (C) 2004 Published by Elsevier Ltd.
引用
收藏
页码：5031 / 5040
页数：10
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