Regioselective reactions of organozinc reagents with 2,4-dichloroquinoline and 5,7-dichloropyrazolo[1,5-a]pyrimidine

被引：44

作者：

Shiota, T ^{[1
]}

Yamamori, T ^{[1
]}

机构：

[1] Shionogi & Co Ltd, Shionogi Res Labs, Fukushima Ku, Osaka 5530002, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 02期

关键词：

D O I：

10.1021/jo981423a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Strategies for controlling the regioselective reactions between 2,4-dichloroquinoline and organozinc reagents are described. 2,4-Dichloroquinoline has been found to react with benzylic zinc and phenylzinc reagents in the presence of catalytic amounts of palladium complexes to exclusively give a-substituted products. Several metal salts were examined as an additive for gamma-selective coupling reactions. The most effective additive for selective coupling reaction at the gamma-position has been found to be LiCl. These conditions for alpha- or gamma-selective coupling reactions were applied to the reaction between 5,7-dichloropyrazolo[1,5-alpha]pyrimidine and a biphenylmethylzinc reagent in the synthesis of the angiotensin II receptor antagonists. This regioselectivity should be generally applicable to other alpha,gamma-dichloroazine systems.

引用

页码：453 / 457

页数：5

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