Nilesh B. Patil , Rhutuja Patil , Ganesh U. Chaturbhuj
{"title":"NCBSI/TEA: A reagent system for rapid and efficient synthesis of isoxazolines from aldoxime","authors":"Nilesh B. Patil , Rhutuja Patil , Ganesh U. Chaturbhuj","doi":"10.1016/j.tetlet.2025.155489","DOIUrl":null,"url":null,"abstract":"<div><div>This report describes an efficient method for synthesizing isoxazolines from aldoximes using NCBSI as a reagent. In this protocol, <em>N</em>-chloro-<em>N</em>-(phenylsulfonyl)benzene sulfonamide (NCBSI) oxidized aldoximes into nitrile oxide. The nitrile oxide underwent 1,3-dipolar cycloaddition to alkenes, giving isoxazolines in good to excellant yields. Furthermore, the precursor <em>N</em>-(phenylsulfonyl)benzene sulfonamide was recovered and transformed to NCBSI, making the protocol eco-friendly and cost-effective.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155489"},"PeriodicalIF":1.5000,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403925000383","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
This report describes an efficient method for synthesizing isoxazolines from aldoximes using NCBSI as a reagent. In this protocol, N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI) oxidized aldoximes into nitrile oxide. The nitrile oxide underwent 1,3-dipolar cycloaddition to alkenes, giving isoxazolines in good to excellant yields. Furthermore, the precursor N-(phenylsulfonyl)benzene sulfonamide was recovered and transformed to NCBSI, making the protocol eco-friendly and cost-effective.
本文介绍了一种以NCBSI为试剂,以醛肟为原料合成异恶唑啉的有效方法。在这个方案中,n -氯- n -(苯基磺酰基)苯磺酰胺(NCBSI)氧化醛肟生成腈氧化物。将氧化腈与烯烃进行1,3-偶极环加成,得到收率高至优异的异恶唑类化合物。此外,前体N-(苯基磺酰)苯磺酰胺被回收并转化为NCBSI,使该工艺环保且经济高效。
期刊介绍:
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.