Reactions of azepinones with electrophiles

被引：8
作者：
Dubinina, Galyna G. [1 ]
Chain, William J. [1 ,2 ]
机构：
[1] Univ Hawaii, Dept Chem, Honolulu, HI 96822 USA
[2] Univ Hawaii, Ctr Canc, Honolulu, HI 96813 USA
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 08期
关键词：
Azepinone; Isomerization; Ring-expansion; Ring-contraction; Alkylation; Alkyl halide; Epoxide; Synthesis; Alkaloid; DIELS-ALDER REACTIONS;
D O I：
10.1016/j.tetlet.2010.12.091
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Azepinones are available via a one-pot cycloaddition-ring expansion reaction sequence in good yield. The reactions of azepinones with alkyl halides and epoxides were studied. We report herein protocols for the alkylation of azepinones at nitrogen with alkyl halides and epoxides and the isomerizations that occur in the presence of a base. We also report an unexpected ring contraction under oxidative conditions. (C) 2010 Elsevier Ltd. All rights reserved.
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页码：939 / 942
页数：4
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