邻恶唑啉基苯基锂与一氧化碳的反应。通过芳酰基锂中间体的羰基化环化反应。

Reaction of o-oxazolinylphenyllithium with carbon monoxide. Carbonylative cyclization via an aroyllithium intermediate.

作者信息

Iwamoto K, Chatani N, Murai S

机构信息

Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.

出版信息

J Org Chem. 2000 Nov 17;65(23):7944-8. doi: 10.1021/jo000977m.

DOI:10.1021/jo000977m

PMID:11073602

Abstract

The carbonylation of a phenyllithium containing an oxazoline group at the ortho position, followed by quenching with water, afforded a tricyclic compound, 3,3-dimethyl-2,3-dihydrooxazolo[2, 3-a]isoindol-5(9bH)-one, in 91% yield. This reaction proceeded via an intramolecular cyclization of the aroyllithium species, to give the tricyclic dienolate. Treatment of the tricyclic dienolate with electrophiles, such as alkyl halides, aldehydes, ketones, and epoxides gave the substituted oxazolo[2,3-a]isoindolinones in good yield.

摘要

邻位含有恶唑啉基团的苯基锂进行羰基化反应，随后用水淬灭，以91%的产率得到三环化合物3,3-二甲基-2,3-二氢恶唑并[2,3-a]异吲哚-5(9bH)-酮。该反应通过芳酰基锂物种的分子内环化进行，生成三环二烯醇盐。用亲电试剂如卤代烃、醛、酮和环氧化合物处理三环二烯醇盐，以良好的产率得到取代的恶唑并[2,3-a]异吲哚啉酮。