Intouch Rakchaya, Phanida Thongaram, Sengchan Saiyalard, Kredmanee Yimnoi, W. Wattanathana, Nutthawat Chuanopparat, P. Ngernmeesri
{"title":"Unexpected one-pot synthesis of 3-cinnamoyl-3-hydroxyphthalide derivatives","authors":"Intouch Rakchaya, Phanida Thongaram, Sengchan Saiyalard, Kredmanee Yimnoi, W. Wattanathana, Nutthawat Chuanopparat, P. Ngernmeesri","doi":"10.1055/a-2312-0444","DOIUrl":null,"url":null,"abstract":"A new and simple method to prepare 3-cinnamoyl-3-hydroxyphthalide derivatives from 2-hydroxy-3-methyl-1,4-naphthoquinone and substituted benzaldehydes was unexpectedly uncovered. The reaction was conveniently performed in DMSO at 100 ⁰C with K3PO4 as a base and AlCl3 as a catalyst. We proposed that the products occurred via a cascade process involving nucleophilic addition followed by demethylation and rearrangement. The products were typically obtained in moderate to good yields. The highest yield (95%) was obtained when the reaction of 2-bromobenzaldehyde was performed for 24 hours. X-ray crystallography of the product derived from 2-fluorobenzaldehyde unequivocally confirmed the structures of the hydroxyphthalide derivatives.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"87 10","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synlett","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/a-2312-0444","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
A new and simple method to prepare 3-cinnamoyl-3-hydroxyphthalide derivatives from 2-hydroxy-3-methyl-1,4-naphthoquinone and substituted benzaldehydes was unexpectedly uncovered. The reaction was conveniently performed in DMSO at 100 ⁰C with K3PO4 as a base and AlCl3 as a catalyst. We proposed that the products occurred via a cascade process involving nucleophilic addition followed by demethylation and rearrangement. The products were typically obtained in moderate to good yields. The highest yield (95%) was obtained when the reaction of 2-bromobenzaldehyde was performed for 24 hours. X-ray crystallography of the product derived from 2-fluorobenzaldehyde unequivocally confirmed the structures of the hydroxyphthalide derivatives.