New strategies for the synthesis of fluorinated vinylogous amidines and β-enamino ketones

被引：53

作者：

Fustero, S ^{[1
]}

de la Torre, MG ^{[1
]}

Pína, B ^{[1
]}

Fuentes, AS ^{[1
]}

机构：

[1] Univ Valencia, Fac Farm, Dept Quim Organ, Valencia 46100, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 15期

关键词：

D O I：

10.1021/jo990392w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of fluorinated imidoyl chlorides 3 with ketimines 1a provides fluorinated 1,3-diimines, which were exclusively isolated as vinylogous amidine tautomers 2 beta, with good yields. Fluorinated beta-enamino ketones 4 are obtained by regioselective hydrolysis of 2. Complementary methods for the synthesis of regioisomeric beta-enamino ketones 4 and 5 are also reported. These methods include the reaction of azaenolates of ketimines with fluorinated esters 6 and reactions of ketone enolates with fluorinated imidoyl chlorides 3. The behavior of these systems in hydrolysis reactions was also tested.

引用

页码：5551 / 5556

页数：6

共 48 条

[1]

[Anonymous], 1991, Fluorine in Bioorganic Chemistry

[2] SYNTHESIS OF DIIMINES FROM 1,2-DICARBONYL COMPOUNDS BY DIRECT CATALYZED CONDENSATION [J].