Biginelli condensations of fluorinated 3-oxo esters and 1,3-diketones [1]

被引：83

作者：

Saloutin, VI

Burgart, YV

Kuzueva, OG

Kappe, CO

Chupakhin, ON

机构：

[1] Russian Acad Sci, Inst Organ Synth, UD, Ekaterinburg 620219, Russia

[2] Karl Franzens Univ Graz, Inst Organ Chem, A-8010 Graz, Austria

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2000年 / 103卷 / 01期

关键词：

fluoroalkyl 3-oxo esters and 1,3-diketones; Biginelli reaction; hexahydropyrimidines;

D O I：

10.1016/S0022-1139(99)00216-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Condensation of fluorinated 3-oxo esters or 1,3-diketones with benzaldehyde and (thio)urea results in the diastereoselective formation of 4-fluoroalkyl-4-hydroxy-2-oxo(thioxo)-6-phenyl-hexahydropyrimidine-5-carboxylates from which by dehydration under acidic conditions the corresponding 6-fluoroalkyl-2-oxo(thioxo)-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylates were obtained. Under the same conditions, hexafluoroacetylacetone furnishes 4,6-dihydroxy-4,6-di(trifluoromethyl)-hexahydropyrimidin-2-one Some further reactions of these pyrimidine derivatives leading to fused heterocycles are described. (C) 2000 Elsevier Science S.A. All rights reserved.

引用

页码：17 / 23

页数：7

共 14 条

[1]

AKHTAR MS, 1987, INDIAN J CHEM B, V26, P556

[2] Synthesis of fluorinated 2(3)-arylhydrazones of 1,2,3-tri(1,2,3,4-tetra)carbonyl compounds and their heterocyclization reactions [J].