Synthesis of substituted 3,4-dihydropyrimidin-2(1H)-ones and pyrimidin-2(1H)-ones by the Biginelli reaction with 3,5-Di-tert-butyl-4-hydroxybenzaldehyde

被引：8
|
作者：
Sedova, V. F. [1 ]
Krivopalov, V. P. [1 ]
Shkurko, O. P. [1 ]
机构：
[1] Russian Acad Sci, Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Div, Novosibirsk 630090, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 45卷 / 10期
关键词：
DERIVATIVES; ANTIOXIDANTS; AGENTS;
D O I：
10.1134/S1070428009100200
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Three-component acid-catalyzed cyclocondensation of 3,5-di-tret-butyl-4-hydroxybenzaldehyde with urea and ethyl acetoacetate or alpha-nitroacetophenone (Biginelli reaction) under homogeneous conditions gave the corresponding 5-substituted 3,4-dihydropyrimidin-2(1H)-ones having in position 4 of the heteroring an aryl substituent with sterically shielded hydroxy group. The condensation catalyzed by inorganic salts (Fe3+, Co2+, Zn2+, Li+) was successful only with ethyl acetoacetate as initial methylene-active component. Under analogous conditions, acetophenone and 4-fluoroacetophenone gave rise to 4,6-diarylpyrimidin-2(1H)-ones which are capable of undergoing phenol-quinonemethide tautomerism.
引用
收藏
页码：1535 / 1540
页数：6
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