Improved Arndt-Eistert Synthesis of α-Diazoketones Requiring Minimal Diazomethane in the Presence of Calcium Oxide as Acid Scavenger

被引：63

作者：

Pace, Vittorio ^{[1
]}

Verniest, Guido ^{[2
]}

Sinisterra, Josep-Vicent ^{[1
]}

Alcantara, Andres R. ^{[1
]}

De Kimpe, Norbert ^{[2
]}

机构：

[1] Univ Complutense Madrid, Organ & Pharmaceut Chem Dept, Fac Pharm, E-28040 Madrid, Spain

[2] Univ Ghent, Dept Organ Chem, Fac Biosci Engn, B-9000 Ghent, Belgium

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 16期

关键词：

H INSERTION REACTIONS; DIAZO-KETONES; DIAZOCARBONYL COMPOUNDS; ORGANIC-SYNTHESIS; BETA-LACTAMS; TRIMETHYLSILYLDIAZOMETHANE; REAGENT; DERIVATIVES; ACETOLYSIS; CONVERSION;

D O I：

10.1021/jo101105g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical methodology to obtain alpha-diazoketones through an improved Arndt-Eistert synthesis is described. The method allows the efficient transformation of acid halides using a stoichiometric amount of diazomethane in the presence of calcium oxide, without concomitant ketene or haloketone formation. The obtained alpha'-brominated-alpha-diazoketones were employed as suitable substrates for the synthesis of interesting alpha-arylamino-alpha'-halomethylketones.

引用

页码：5760 / 5763

页数：4

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