{"title":"Retro-aza-Henry-type conversion of β-nitrostyrenes to the related hydrazones using ascorbic acid-functionalized graphene as a catalyst","authors":"Hossein Tavakol, Nabiallah Abdollahi","doi":"10.1007/s13738-025-03194-z","DOIUrl":null,"url":null,"abstract":"<div><p>In a present report, a new method is developed for the conversion of β-nitrostyrenes and β-methyl-β-nitrostyrenes to their related hydrazones via a retro-aza-Henry-type conversion. Ascorbic acid-modified graphene oxide was used as an inexpensive, biocompatible, and metal-free catalyst for this reaction which catalyzed the reaction including the C=C double-bond breaking. Via this reaction, 20 different nitroolefin derivatives were successfully converted to the related hydrazones using 3 equivalents of hydrazine hydrate, 3 mL ethanol as a solvent, and 0.01 g catalyst in 4 h at room temperatures. The obtained yields were excellent and it was between 85 and 100% using both electron-releasing and electron-withdrawing groups in different positions. Moreover, the existence of methyl group at the beta position of the β-nitrostyrenes has no negative effect on the reaction. The synthesized catalyst showed appropriate recoverability, with only a 15% reduction in its efficiency after four runs.</p><h3>Graphical abstract</h3>\n<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":676,"journal":{"name":"Journal of the Iranian Chemical Society","volume":"22 4","pages":"877 - 887"},"PeriodicalIF":2.2000,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of the Iranian Chemical Society","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s13738-025-03194-z","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
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Abstract
In a present report, a new method is developed for the conversion of β-nitrostyrenes and β-methyl-β-nitrostyrenes to their related hydrazones via a retro-aza-Henry-type conversion. Ascorbic acid-modified graphene oxide was used as an inexpensive, biocompatible, and metal-free catalyst for this reaction which catalyzed the reaction including the C=C double-bond breaking. Via this reaction, 20 different nitroolefin derivatives were successfully converted to the related hydrazones using 3 equivalents of hydrazine hydrate, 3 mL ethanol as a solvent, and 0.01 g catalyst in 4 h at room temperatures. The obtained yields were excellent and it was between 85 and 100% using both electron-releasing and electron-withdrawing groups in different positions. Moreover, the existence of methyl group at the beta position of the β-nitrostyrenes has no negative effect on the reaction. The synthesized catalyst showed appropriate recoverability, with only a 15% reduction in its efficiency after four runs.
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JICS is an international journal covering general fields of chemistry. JICS welcomes high quality original papers in English dealing with experimental, theoretical and applied research related to all branches of chemistry. These include the fields of analytical, inorganic, organic and physical chemistry as well as the chemical biology area. Review articles discussing specific areas of chemistry of current chemical or biological importance are also published. JICS ensures visibility of your research results to a worldwide audience in science. You are kindly invited to submit your manuscript to the Editor-in-Chief or Regional Editor. All contributions in the form of original papers or short communications will be peer reviewed and published free of charge after acceptance.
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