Reactions of alkyl diazoacetates with pyridinium ylides

被引：0

作者：

Tomilov Yu.V. ^{[1
]}

Platonov D.N. ^{[1
]}

Dorokhov D.V. ^{[1
]}

Nefedov O.M. ^{[1
]}

机构：

[1] N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow

来源：

Russian Chemical Bulletin | 2005年 / 54卷 / 4期

基金：

俄罗斯基础研究基金会;

关键词：

Alkyl diazoacetates; Functionalized diazadienes and azines; Pyridinium ylides; Tetra(methoxycarbonyl)pyrrole; Tetrahydropyridazines;

D O I：

10.1007/s11172-005-0349-6

中图分类号：

学科分类号：

摘要：

Pyridinium (methoxycarbonyl)methylide generated from (methoxycarbonyl) methyl-pyridinium halides under the action of K2CO3 reacts with alkyl diazoacetates in CH2Cl2 at 20°C, resulting in the successive addition of three CHCOOMe fragments from the ylide to form 3,6-bis(alkoxycarbonyl)-4,5-diazaoctadienoic acid diesters. Heating of the latter in the presence of pyridine leads to their isomerization to give tetraalkyl tetrahydropyridazine-tetracarboxylates in high yields. Under more drastic conditions (refluxing xylene in the presence of pyridine), the acyclic tetraesters undergo another transformation to form pyrrole-tetracarboxylic acid esters in yields of up to 60%. © 2005 Springer Science+Business Media, Inc.

引用

页码：1008 / 1012

页数：4

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