Synthesis of N-Alkyl-1,3-dihydro-2,1-benzisoxazoles

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-11-05 DOI:10.1021/acs.orglett.4c03509

Thomas D. Beckler, David Crich

引用次数: 0

Abstract

We describe a practical method for the synthesis of various substituted N-alkyl-1,3-dihydro-2,1-benzisoxazoles and their 2,1-benzisoxazolone precursors starting from readily available methyl 2-nitrobenzoates. The method entails partial nitro reduction with hydrazine and rhodium on carbon to give the hydroxylamines, followed by base-mediated cyclization to give the corresponding benzisoxazol-3(1H)-ones. Subsequent alkylation is conducted under basic conditions and is followed by reduction to the target 1,3-dihydrobenzisoxazoles, achieved with lithium aluminum hydride in the presence of trimethylsilyl chloride.

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合成 N-烷基-1,3-二氢-2,1-苯并异噁唑

我们介绍了一种实用的方法，可以从容易获得的 2-硝基苯甲酸甲酯开始，合成各种取代的 N-烷基-1,3-二氢-2,1-苯并异噁唑及其 2,1-苯并异噁唑酮前体。该方法需要先用肼和碳上铑进行部分硝基还原，得到羟胺，然后在碱介导下进行环化，得到相应的苯并异噁唑-3(1H)-酮。随后在碱性条件下进行烷基化，然后在三甲基氯硅烷存在下用氢化铝锂还原成目标 1,3-二氢苯并异噁唑。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.