A. S. Golubev, I. M. Golubev, P. N. Ostapchuk, T. V. Strelkova, K. Yu. Suponitsky, N. D. Chkanikov
{"title":"Synthesis of 4-(trifluoromethyl)thiocoumarins","authors":"A. S. Golubev, I. M. Golubev, P. N. Ostapchuk, T. V. Strelkova, K. Yu. Suponitsky, N. D. Chkanikov","doi":"10.1007/s11172-024-4421-5","DOIUrl":null,"url":null,"abstract":"<div><p>A convenient method for the synthesis of poorly studied 4-(trifluoromethyl)thiocoumarins from 1-[2-(<i>tert</i>-butylthio)phenyl]-2,2,2-trifluoroethanones was developed. Thiopyranone core of 4-(trifluoromethyl)thiocoumarins was constructed by S-acylation of 1-[2-(<i>tert</i>-butylthio)phenyl]-2,2,2-trifluoroethanones with bromoacetyl bromide followed by treatment with triphenylphosphine to give the phosphonium salt and subsequent intramolecular Wittig reaction. S-Acylation of these substrates with acetyl chlorides bearing active methylene group and subsequent intramolecular Knövenagel condensation gave 3-substituted 4-(trifluoromethyl)thiocoumarins.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 10","pages":"3045 - 3054"},"PeriodicalIF":1.7000,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Chemical Bulletin","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s11172-024-4421-5","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
A convenient method for the synthesis of poorly studied 4-(trifluoromethyl)thiocoumarins from 1-[2-(tert-butylthio)phenyl]-2,2,2-trifluoroethanones was developed. Thiopyranone core of 4-(trifluoromethyl)thiocoumarins was constructed by S-acylation of 1-[2-(tert-butylthio)phenyl]-2,2,2-trifluoroethanones with bromoacetyl bromide followed by treatment with triphenylphosphine to give the phosphonium salt and subsequent intramolecular Wittig reaction. S-Acylation of these substrates with acetyl chlorides bearing active methylene group and subsequent intramolecular Knövenagel condensation gave 3-substituted 4-(trifluoromethyl)thiocoumarins.
期刊介绍:
Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections:
General and Inorganic Chemistry;
Physical Chemistry;
Organic Chemistry;
Organometallic Chemistry;
Chemistry of Natural Compounds and Bioorganic Chemistry.