{"title":"Cs2CO3‐I2 Promoted Efficient Synthesis of Flavones and Flavanones: Total Synthesis of Narengenin and Apigenin","authors":"Kailas Arjun Chavan , Dr. Rohan D. Erande","doi":"10.1002/ejoc.202401298","DOIUrl":null,"url":null,"abstract":"<div><div>Flavonoids are an important class of naturally existing scaffolds known for their diverse biological activities and have been immensely synthesized using stoichiometric reagent amounts. Herein, we report a reliable, robust, one‐pot, transition metal and additive‐free protocol for the synthesis of flavones and flavanones from 2‐hydroxyacetophenone and substituted aldehydes. Our developed method utilizes Cs<sub>2</sub>CO<sub>3</sub> as a base and iodine as an oxidant in H<sub>2</sub>O: DMSO (9 : 1) solvent system, which provides direct access to many flavones and flavanones in excellent yields under milder reaction conditions with simple yet easily available substrates. In application, naturally occurring compounds such as naringenin and apigenin have been successfully synthesized using developed protocol.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 9","pages":"Article e202401298"},"PeriodicalIF":2.5000,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"European Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1434193X25000350","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Flavonoids are an important class of naturally existing scaffolds known for their diverse biological activities and have been immensely synthesized using stoichiometric reagent amounts. Herein, we report a reliable, robust, one‐pot, transition metal and additive‐free protocol for the synthesis of flavones and flavanones from 2‐hydroxyacetophenone and substituted aldehydes. Our developed method utilizes Cs2CO3 as a base and iodine as an oxidant in H2O: DMSO (9 : 1) solvent system, which provides direct access to many flavones and flavanones in excellent yields under milder reaction conditions with simple yet easily available substrates. In application, naturally occurring compounds such as naringenin and apigenin have been successfully synthesized using developed protocol.
期刊介绍:
The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies.
The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry:
Liebigs Annalen
Bulletin des Sociétés Chimiques Belges
Bulletin de la Société Chimique de France
Gazzetta Chimica Italiana
Recueil des Travaux Chimiques des Pays-Bas
Anales de Química
Chimika Chronika
Revista Portuguesa de Química
ACH—Models in Chemistry
Polish Journal of Chemistry.