{"title":"Selective Access to Sultams and Spirocyclic Sultams by the Divergent Annulations of (N‐Aryl)‐Alkynyl Sulphonamides","authors":"Chada Raji Reddy , Anjali Rathaur , Banoth Karuna Sagar , Agnuru Theja , Amol D. Patil , Muppidi Subbarao","doi":"10.1002/adsc.202400382","DOIUrl":null,"url":null,"abstract":"<div><div>Herein, we present the first annulation reaction of (<em>N</em>‐aryl)‐alkynyl sulphonamides leading to sultams or spirocyclic sultams. The selective formation of aforesaid products is based on the variable reactivity, intramolecular <em>ortho</em>‐cyclization or dearomative <em>ipso</em>‐annulation, guided by the substituent on <em>N</em>‐aryl group of the substrate. The <em>ortho</em>‐annulation is mediated by electrophile, while the <em>ipso</em>‐annulation is promoted by the radical, enabling the functionalization (selenyl or iodo) on sultams. The synthetic potential of this method is illustrated by modifications of the functional groups present in the products obtained.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"366 22","pages":"Pages 4772-4777"},"PeriodicalIF":4.4000,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S161541502400311X","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, we present the first annulation reaction of (N‐aryl)‐alkynyl sulphonamides leading to sultams or spirocyclic sultams. The selective formation of aforesaid products is based on the variable reactivity, intramolecular ortho‐cyclization or dearomative ipso‐annulation, guided by the substituent on N‐aryl group of the substrate. The ortho‐annulation is mediated by electrophile, while the ipso‐annulation is promoted by the radical, enabling the functionalization (selenyl or iodo) on sultams. The synthetic potential of this method is illustrated by modifications of the functional groups present in the products obtained.
期刊介绍:
Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry.
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