{"title":"Hydrogen bond assisted reactivity of Ylidineketonitriles with 1° amines: A chemoselective synthesis of 2-pyridone and 2-aminopyridine derivatives","authors":"Damodar Karuturi , Mahesh Kalbagh , Prashantha Kamath , Venunath Hapse , Alok Kumar Pandey , Mark Montgomery , Mukul Lal","doi":"10.1080/00397911.2024.2385567","DOIUrl":null,"url":null,"abstract":"<div><p>Ylidineketonitrile <strong>2</strong> with chlorodifluoromethyl (A = Cl) demonstrated a strong solvent dependence reaction with primary amines to form either 1-<em>N</em>-alkylated-3,5-disubstituted-2-pyridones or 2-<em>N</em>-alkylated-3, 5-trisubstituted pyridines. The methodology was tested for its scope with primary amines and synthesized 29 derivatives in good to excellent yield. Ylidineketonitrile <strong>2e</strong> preferrentially forms pyridone derivatives in the majority of the solvents screened except trifluoroethanol, where chemoselective formation of 2-aminopyridine derivatives was observed.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 16","pages":"Pages 1344-1353"},"PeriodicalIF":1.8000,"publicationDate":"2024-08-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthetic Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S0039791124000766","RegionNum":3,"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
Ylidineketonitrile 2 with chlorodifluoromethyl (A = Cl) demonstrated a strong solvent dependence reaction with primary amines to form either 1-N-alkylated-3,5-disubstituted-2-pyridones or 2-N-alkylated-3, 5-trisubstituted pyridines. The methodology was tested for its scope with primary amines and synthesized 29 derivatives in good to excellent yield. Ylidineketonitrile 2e preferrentially forms pyridone derivatives in the majority of the solvents screened except trifluoroethanol, where chemoselective formation of 2-aminopyridine derivatives was observed.
期刊介绍：
Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.
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