{"title":"Comparison of metal-carbenoid reactions of β-2-five-membered heteroaryl substituted α,β-unsaturated ketones.","authors":"Kumsal Eroğlu, Olcay Anaç, Füsun Şeyma Kişkan","doi":"10.55730/1300-0527.3625","DOIUrl":null,"url":null,"abstract":"<p><p>In this study, <i>β</i>-2-heteroaryl substituted (<i>N</i>-methyl 2-pyrrolyl, 2-thiophenyl, 2-furyl) <i>α</i>,<i>β</i>-unsaturated ketones were reacted with two <i>α</i>-diazo carbonyl compounds that had different characteristics (dimethyl diazo malonate and 1-diazo-1-phenyl-propane-2-one) in the presence of both copper and rhodium catalysts. In the case of reactions with <i>N</i>-methyl 2-pyrrolyl <i>α</i>,<i>β</i>-unsaturated ketones, the major product was the insertion derivative. However, in the reactions of 2-thiophenyl and 2-furyl <i>α</i>,<i>β</i>-unsaturated ketones with dimethyl diazomalonate (acceptor-acceptor disubstituted), only dihydrofuran products were formed over carbonyl ylides. When 2-thiophenyl and 2-furyl <i>α</i>,<i>β</i>-unsaturated ketones were reacted with 1-diazo-1-phenyl-propane-2-one (donor-acceptor disubstituted), 1-phenylpropane-1,2-dione was obtained under our reaction conditions.</p>","PeriodicalId":23367,"journal":{"name":"Turkish Journal of Chemistry","volume":null,"pages":null},"PeriodicalIF":1.3000,"publicationDate":"2023-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10965174/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Turkish Journal of Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.55730/1300-0527.3625","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2023/1/1 0:00:00","PubModel":"eCollection","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
In this study, β-2-heteroaryl substituted (N-methyl 2-pyrrolyl, 2-thiophenyl, 2-furyl) α,β-unsaturated ketones were reacted with two α-diazo carbonyl compounds that had different characteristics (dimethyl diazo malonate and 1-diazo-1-phenyl-propane-2-one) in the presence of both copper and rhodium catalysts. In the case of reactions with N-methyl 2-pyrrolyl α,β-unsaturated ketones, the major product was the insertion derivative. However, in the reactions of 2-thiophenyl and 2-furyl α,β-unsaturated ketones with dimethyl diazomalonate (acceptor-acceptor disubstituted), only dihydrofuran products were formed over carbonyl ylides. When 2-thiophenyl and 2-furyl α,β-unsaturated ketones were reacted with 1-diazo-1-phenyl-propane-2-one (donor-acceptor disubstituted), 1-phenylpropane-1,2-dione was obtained under our reaction conditions.
期刊介绍:
The Turkish Journal of Chemistry is a bimonthly multidisciplinary journal published by the Scientific and Technological Research Council of Turkey (TÜBİTAK).
The journal is dedicated to dissemination of knowledge in all disciplines of chemistry (organic, inorganic, physical, polymeric, technical, theoretical and analytical chemistry) as well as research at the interface with other sciences especially in chemical engineering where molecular aspects are key to the findings.
The journal accepts English-language original manuscripts and contribution is open to researchers of all nationalities.
The journal publishes refereed original papers, reviews, letters to editor and issues devoted to special fields.
All manuscripts are peer-reviewed and electronic processing ensures accurate reproduction of text and data, plus publication times as short as possible.