Oxidative synthesis of azacyclic derivatives through the nitrenium ion: application of a hypervalent iodine species electrochemically generated from iodobenzene

被引：71

作者：

Amano, Yoshiharu ^{[1
]}

Nishiyama, Shigeru ^{[1
]}

机构：

[1] Keio Univ, Fac Sci & Technol, Dept Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 37期

关键词：

quinolinone; azaspiro[4.5]decane; hypervalent iodine; anodic oxidation;

D O I：

10.1016/j.tetlet.2006.07.050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidation of the methoxyamide derivatives 1, 4, and 7 has been examined to elaborate efficient synthetic methodology of the azacyclic derivatives 2, 3, 5, 6, and 8, which would be applicable as synthetic intermediates of complicated bioactive substances. In addition to direct anodic and PIFA [phenyliodine(III) bis(trifluoroacetate)] oxidations, an active species derived from iodobenzene generated under electrolytic conditions was examined as an oxidant, and its synthetic efficacy was demonstrated in comparison of the reaction outcomes with other oxidation methods. In the oxidation, the methoxy substitution of substrates modulated the cyclization mode to provide the azaspiro- (2, 8) or quinolinone-type (3, 5, 6) products. (c) 2006 Published by Elsevier Ltd.

引用

页码：6505 / 6507

页数：3

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