Chemical and electrocatalytic cascade cyclization of Guareschi imides: 'one-pot' simple and efficient way to the 2,4-dioxo-3-azabicyclo[3.1.0]hexane scaffold

被引：20

作者：

Vereshchagin, Anatoly N. ^{[1
]}

Elinson, Michail N. ^{[1
]}

Dorofeeva, Evgeniya O. ^{[1
]}

Demchuk, Dmitry V. ^{[1
]}

Bushmarinov, Ivan S. ^{[2
]}

Goloveshkin, Alexander S. ^{[2
]}

Nikishin, Gennady I. ^{[1
]}

机构：

[1] ND Zelinskii Inst Organ Chem, Moscow 119991, Russia

[2] AN Nesmeyanov Inst Organoelement Cpds, Moscow 119991, Russia

来源：

TETRAHEDRON | 2013年 / 69卷 / 25期

基金：

俄罗斯基础研究基金会;

关键词：

Electrolysis; Electrocatalysis; Mediator; Sodium bromide; Guareschi imides; Cyclization; 3-Azabicyclo[3.1.0]hexanes; ELECTROCHEMICAL TRANSFORMATION; MULTICOMPONENT REACTIONS; SUBSTITUTED CYCLOPROPANES; SPIRO-COMPOUNDS; MALONONITRILE; MALONATE; DERIVATIVES; STABILITY; ACIDS; (+/-)-ALPHA-ISOSPARTEINE;

D O I：

10.1016/j.tet.2013.04.035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electrolysis of Guareschi imides in alcohol in an undivided cell in the presence of sodium bromide as mediator results in fast and efficient cyclization with formation of a substituted 3-azabicyclo[3.1.0] hexane system in 80-98%. The fast (30 min) electrocatalytic reaction proceeds smoothly under neutral and mild conditions. The use of electrocatalysis in a cascade cyclization reaction is an efficient approach to the medicinally relevant 3-azabicyclo[3.1.0]hexane scaffold avoiding the inconvenient direct use of molecular halogen or halogenated substrates, and is also beneficial from the viewpoint of diversity-orientated large-scale processes. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：5234 / 5241

页数：8

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