Feng-Ting Liu , Shuo Wang , Yong-Shun Chen , Jun-Ying Miao , Bao-Xiang Zhao , Zhao-Min Lin
{"title":"新型亚胺酸盐作为多功能有机荧光材料的简便一步法合成","authors":"Feng-Ting Liu , Shuo Wang , Yong-Shun Chen , Jun-Ying Miao , Bao-Xiang Zhao , Zhao-Min Lin","doi":"10.1039/d4qo01628a","DOIUrl":null,"url":null,"abstract":"<div><div>Imidates have enormous applications in the synthesis of natural products and nitrogen-containing heterocyclic compounds, as well as in drug development. However, there is currently a lack of green and efficient synthesis methods for imidate compounds. We present a novel one-pot synthesis of multifunctional organic fluorescent imidates from quinolinium salt derivatives, nitrosoarenes and alcohols. This method has the advantages of operational simplicity, mild reaction conditions, metal-free catalysis, a wide substrate scope (43 examples) and excellent isolated yields (up to 93%). Meanwhile, quinolinium-imidates exhibit good fluorescence intensity and excellent chemical stability, which makes them suitable for application in living cells, and in particular, imidate can target the endoplasmic reticulum with high selectivity.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 1","pages":"Pages 97-105"},"PeriodicalIF":0.0000,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Facile one-pot synthesis of novel imidates as multifunctional organic fluorescent materials†\",\"authors\":\"Feng-Ting Liu , Shuo Wang , Yong-Shun Chen , Jun-Ying Miao , Bao-Xiang Zhao , Zhao-Min Lin\",\"doi\":\"10.1039/d4qo01628a\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Imidates have enormous applications in the synthesis of natural products and nitrogen-containing heterocyclic compounds, as well as in drug development. However, there is currently a lack of green and efficient synthesis methods for imidate compounds. We present a novel one-pot synthesis of multifunctional organic fluorescent imidates from quinolinium salt derivatives, nitrosoarenes and alcohols. This method has the advantages of operational simplicity, mild reaction conditions, metal-free catalysis, a wide substrate scope (43 examples) and excellent isolated yields (up to 93%). Meanwhile, quinolinium-imidates exhibit good fluorescence intensity and excellent chemical stability, which makes them suitable for application in living cells, and in particular, imidate can target the endoplasmic reticulum with high selectivity.</div></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"12 1\",\"pages\":\"Pages 97-105\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-10-28\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S2052412924007599\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/10/30 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052412924007599","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/10/30 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
Facile one-pot synthesis of novel imidates as multifunctional organic fluorescent materials†
Imidates have enormous applications in the synthesis of natural products and nitrogen-containing heterocyclic compounds, as well as in drug development. However, there is currently a lack of green and efficient synthesis methods for imidate compounds. We present a novel one-pot synthesis of multifunctional organic fluorescent imidates from quinolinium salt derivatives, nitrosoarenes and alcohols. This method has the advantages of operational simplicity, mild reaction conditions, metal-free catalysis, a wide substrate scope (43 examples) and excellent isolated yields (up to 93%). Meanwhile, quinolinium-imidates exhibit good fluorescence intensity and excellent chemical stability, which makes them suitable for application in living cells, and in particular, imidate can target the endoplasmic reticulum with high selectivity.