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.

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收藏

页码：5031 / 5040

页数：10

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