Synthesis of endocyclic enol methyl ethers of 3-acylthiotetronic acids and their reactions with amines

被引：6

作者：

Budnikova, MV ^{[1
]}

Rubinov, DB ^{[1
]}

机构：

[1] Byelarussian Acad Sci, Inst Bioorgan Chem, Minsk 220141, BELARUS

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 37卷 / 10期

关键词：

Acetone; Acetyl; Dione; Enol; Diazomethane;

D O I：

10.1023/A:1013464314542

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acylation of (3H,5H)-tetrahydrothiophene-2,4-dione (thiotetronic acid) with acetyl, propionyl, and valeryl chlorides followed by O-C isomerization in the presence of 4-dimethylaminopyridine or acetone cyanohydrin gave rise to 3-acetyl, 3-propanoyl, and 3-pentanoyl derivatives of thiotetronic acid. The reaction of 3-acylthiotetronic acids with diazomethane afforded enol methyl ethers at the endocyclic keto groups. The subsequent reaction of these enol ethers with allylamine, benzylamine, and p-anisidine occurs along the mechanism of vinylog substitution providing the corresponding endocyclic enamino derivatives.

引用

页码：1478 / 1485

页数：8

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