SYNTHESES OF 3-METHYLPYRROLE VIA METHYL 4-METHYLPYRROLE-2-CARBOXYLATE - A THERMAL OXAZOLONE PYRONE REARRANGEMENT

被引：10

作者：

CORNFORTH, J ^{[1
]}

DU, MH ^{[1
]}

机构：

[1] BEIJING MED UNIV, BEIJING, PEOPLES R CHINA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 05期

关键词：

D O I：

10.1039/p19900001459

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Ethoxy-2-methylpropenal with hippuric acid and acetic anhydride gave 4-(3-ethoxy-2-methylallylidene)-2-phenyloxazol-5(4H)-one. By successive treatment with methanolic potassium hydroxide, acetic-hydrochloric acid, and methanolic sodium methoxide, methyl 4-methylpyrrole-2-carboxylate was formed in high overall yield, and was converted into 3-methylpyrrole by hydrolysis and decarboxylation. The oxazolone with sodium hydroxide in acetone or dioxane gave 4-(3-hydroxy-2-methylallylidene)-2-phenyloxazol-5(4H)-one, isomerized in boiling acetone, or on melting, to 3-benzoylamino-5-methylpyran-2-one. 3-Ethoxy-2-methylpropenal condensed with glycine methyl ester to give an enaminal, cyclized in moderate yield to methyl 4-methylpyrrole-2-carboxylate.

引用

页码：1459 / 1462

页数：4