One-Pot Synthesis of α-Alkylidene-γ-butyrolacton-2-ones (Tetronic Acid Derivatives): Polar Solvent Induces a New Type of γ-Lactonization

被引：9

作者：

Alizadeh, Abdolali ^{[1
]}

Sabahnoo, Hamideh ^{[1
]}

Noaparast, Zohreh ^{[1
]}

Zohreh, Nasrin ^{[1
]}

Mikaeili, Azadeh ^{[1
]}

机构：

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

来源：

SYNLETT | 2010年 / 12期

关键词：

gamma-lactone; alpha-alkylidene-gamma-butyrolactone; tetronic acid; enaminone; chloroacetyl chloride; polar solvent; one-pot multicomponent reaction; BUTYROLACTONE DERIVATIVES; STEREOSELECTIVE-SYNTHESIS; CROSS-METATHESIS; LACTONES; INHIBITORS; OLEFINS; AMINE;

D O I：

10.1055/s-0030-1258113

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

An efficient, one-pot synthetic protocol toward alpha-alkylidene-gamma-butyrolacton-2-ones, a rather unexplored class of heterocyclic scaffolds starting from primary amines, methyl acetoacetate, and chloroacetyl chloride is described. The mixture of MeCN-MeOH as a polar solvent triggers a new cycloaddition of the enaminone intermediate. The reaction is completed within 12 hours under reflux condition to produce the title compounds.

引用

收藏

页码：1854 / 1858

页数：5

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