Lithiation of 1-chloromethylbenzotriazole: Generation and elaboration of benzotriazolyloxiranes

被引：18

作者：

Katritzky, AR ^{[1
]}

Manju, K

Steel, PJ

机构：

[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA

[2] Univ Canterbury, Dept Chem, Christchurch 1, New Zealand

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 02期

关键词：

D O I：

10.1021/jo026400h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-Benzotriazolylchloromethyllithium generated from 1-chloromethylbenzotriazole (1) and LDA reacts with enolizable and nonenolizable ketones to give benzotriazolyloxiranes 2a-g in good yields. The oxiranyllithiums 4a-d generated from 2a-d and n-BuLi at -78 degreesC were trapped by a variety of electrophiles to give oxiranyl derivatives 5a-j in good to excellent yields. Lewis-acid-promoted nucleophilic ring opening of benzotriazolyloxiranes 2a,f,g with allyltrimethylsilane gave the corresponding 1,7-octadien-4-ols 6a-c in 68-75% yield. Hydrolysis of alpha-acylbenzotriazolyloxiranes 5g,h provided 3-hydroxy-1,2-diones 7a and 7b in 73 and 86% yield, respectively.

引用

页码：407 / 411

页数：5

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