General Route to Purin-2-ylmagnesium Halides by Metal-Halogen Exchange in Dichloromethane

被引：2

作者：

Gazzola, Silvia ^{[1
]}

Gordon, Malcolm R. ^{[1
]}

Lindell, Stephen D. ^{[1
]}

机构：

[1] Bayer AG, Crop Sci Div, Ind Pk Hochst, D-65926 Frankfurt, Germany

来源：

SYNLETT | 2020年 / 31卷 / 05期

关键词：

nucleobases; purinylmagnesium halides; Grignard reaction; metal-halogen exchange; dichloromethane; PURIN-6-YL MAGNESIUM HALIDES; PURINES; PYRIMIDINE; SAR;

D O I：

10.1055/s-0039-1690818

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of a solution of a 9-alkyl- or 9-aryl-2-iodopurine in dichloromethane with an ethereal solution of ethylmagnesium bromide at -5 degrees C generates the corresponding purin-2-ylmagnesium bromide, which reacts with aldehydes to give the corresponding 2-(hydroxyalkyl)purines in yields of 53-84%. The purin-2-yl Grignard reagents show good functional-group tolerance to ester and nitro groups, and the method permits the synthesis of the previously unknown 6-unsubstituted 2-magnesiopurines for the first time. Performing the same procedure in THF as solvent resulted either in extensive decomposition or rapid isomerization to give purin-8-ylmagnesium halides.

引用

页码：512 / 516

页数：5

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