Synthesis of diazabicyclo compounds possessing an α-nitrolactam framework

被引：8

作者：

Asahara, Haruyasu ^{[1
,2
]}

Takeda, Shota ^{[1
]}

Saigo, Kazuhiko ^{[1
,2
]}

Nishiwaki, Nagatoshi ^{[1
,2
]}

机构：

[1] Kochi Univ Technol, Sch Environm Sci & Engn, Kami, Kochi 7828502, Japan

[2] Kochi Univ Technol, Res Ctr Mat Sci & Engn, Kami, Kochi 7828502, Japan

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 19期

关键词：

Bicyclic compound; Michael addition; Nitroacetate; Pseudo-intramolecular process;

D O I：

10.1016/j.tetlet.2015.03.100

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diazabicyclo compounds possessing an alpha-nitrolactam framework were directly synthesized upon treatment of alpha-nitro-delta-keto esters with diamines. This reaction proceeds via pseudo-intramolecular process. In this process, the formation of ammonium nitronate is a key step, by which the amino group and the ketone carbonyl group are in close proximity to cause the imine formation efficiently. The following tandem bicyclization constructs 1,7-diaza-3-nitro-2-oxobicyclic systems having two aryl groups at the 4- and 6-positions. (C) 2015 Published by Elsevier Ltd.

引用

页码：2504 / 2507

页数：4

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