Synthesis of Heterocyclic [3.3.3]Propellanes via a Sequential Four-Component Reaction

被引：96

作者：

Alizadeh, Abdolali ^{[1
]}

Rezvanian, Atieh ^{[1
]}

Zhu, Long-Guan ^{[2
]}

机构：

[1] Tarbiat Modares Univ, Dept Chem, Tehran, Iran

[2] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 09期

关键词：

C BOND FORMATION; MULTICOMPONENT REACTIONS; ONE-POT; ALKALOIDS; EFFICIENT; PYRROLES; INDOLES;

D O I：

10.1021/jo300457m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly chemoselective heteroannulation protocol for the synthesis of unreported polysubstituted heterocyclic [3.3.3]propellanes has been developed by sequential four-component reaction of ninhydrin, malononitrile, primary amines, and dialkyl acetylenedicarboxylates under mild conditions in water. To the best of our knowledge, there are no previous reports for the synthesis of these classes of heterocyclic [3.3.3]propellanes. The merit of this sequential Knoevenagel condensation/enamine formation/Michael addition/cydization sequence is highlighted by its high atom-economy, excellent yields, the use of water as reaction media, and the efficiency of production without the use of any activator or metal promoters. This synthesis serves as a nice addition to group-assistant-purification (GAP) chemistry in which purification via chromatography and recrystallization can be avoided, and the pure products were obtained simply by washing the crude products with 95% ethanol.

引用

页码：4385 / 4390

页数：6

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