A novel catalyst for the synthesis of 3–5-disubstituted isoxazole derivatives from aldoximes

IF 2.2 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of the Iranian Chemical Society Pub Date : 2025-01-14 DOI:10.1007/s13738-024-03164-x

Nesimi Uludag, Alper Sanlı

{"title":"A novel catalyst for the synthesis of 3–5-disubstituted isoxazole derivatives from aldoximes","authors":"Nesimi Uludag, Alper Sanlı","doi":"10.1007/s13738-024-03164-x","DOIUrl":null,"url":null,"abstract":"<div><p>An efficient new approach has been described for the synthesis of substituted isoxazole derivatives 3a-l from substituted aldoximes and diethyl acetylenedicarboxylate using NaNO<sub>2</sub> and AlCl<sub>3</sub> in one step in moderate to excellent yields (55–94%). The key nitrile <i>N-</i>oxide intermediates that are required for the synthesis of isoxazole derivatives are formed by treatment of substituted aldoxime with assisted discovery of its newer applications by successive treatment with NaNO<sub>2</sub>. The generated nitrile oxides underwent [3 + 2] dipolar cycloaddition of alkynes over AlCl<sub>3</sub> as a Lewis acid. Moreover, this approach has considerably assisted in the discovery of its significant advantages. This strategy is creating a five-membered ring with an oxygen and nitrogen atom adjacent to each other as either catalyst or reagent. The structures of the synthesized compounds were confirmed by spectroscopic methods, and a mechanism was proposed.</p><h3>Graphical abstract</h3>\n<div><figure><div><div><picture><img></picture></div></div></figure></div></div>","PeriodicalId":676,"journal":{"name":"Journal of the Iranian Chemical Society","volume":"22 3","pages":"509 - 515"},"PeriodicalIF":2.2000,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s13738-024-03164-x.pdf","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of the Iranian Chemical Society","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s13738-024-03164-x","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 0

Abstract

An efficient new approach has been described for the synthesis of substituted isoxazole derivatives 3a-l from substituted aldoximes and diethyl acetylenedicarboxylate using NaNO₂ and AlCl₃ in one step in moderate to excellent yields (55–94%). The key nitrile N-oxide intermediates that are required for the synthesis of isoxazole derivatives are formed by treatment of substituted aldoxime with assisted discovery of its newer applications by successive treatment with NaNO₂. The generated nitrile oxides underwent [3 + 2] dipolar cycloaddition of alkynes over AlCl₃ as a Lewis acid. Moreover, this approach has considerably assisted in the discovery of its significant advantages. This strategy is creating a five-membered ring with an oxygen and nitrogen atom adjacent to each other as either catalyst or reagent. The structures of the synthesized compounds were confirmed by spectroscopic methods, and a mechanism was proposed.

Graphical abstract

Abstract Image

查看原文本刊更多论文

求助全文

约1分钟内获得全文求助全文

来源期刊

Journal of the Iranian Chemical Society 化学-化学综合

CiteScore

4.40

自引率

8.30%

发文量

230

审稿时长

5.6 months

期刊介绍： JICS is an international journal covering general fields of chemistry. JICS welcomes high quality original papers in English dealing with experimental, theoretical and applied research related to all branches of chemistry. These include the fields of analytical, inorganic, organic and physical chemistry as well as the chemical biology area. Review articles discussing specific areas of chemistry of current chemical or biological importance are also published. JICS ensures visibility of your research results to a worldwide audience in science. You are kindly invited to submit your manuscript to the Editor-in-Chief or Regional Editor. All contributions in the form of original papers or short communications will be peer reviewed and published free of charge after acceptance.