{"title":"NaHCO3-promoted Formal [4+3] Annulation of Salicylaldehydes with Isoquinolinium Salts Accessing Isoquinoline-fused Benzo[f][1,3]oxazepines","authors":"Qiang Tang, Yanan Liu, Mengdi Wu, Yangzilin Kong, Xiaochun Jiang, Shizhang Ling, Yongjia Shang, Xinwei He","doi":"10.1002/adsc.202401295","DOIUrl":null,"url":null,"abstract":"A concise and practical sustainable strategy for modular access to isoquinoline-fused benzo[f][1,3]oxazepine derivatives through a formal [4+3] annulation of commercially available salicyaldehydes with isoquinolinium salts has been developed. The reactions proceeded through the formation of two new bonds (C=C and C-O) and a seven-membered heterocyclic ring in one pot. Remarkably, use of simple NaHCO3 as a mild base, open atmosphere, nonhazardous reagents, nice functional group tolerance, and easily scale up are added characteristics to this approach. A wide range of substrates are compatible with this mild reaction system, thereby proving a facile and reliable protocol for constructing a benzo[f][1,3]oxazepine skeletons.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"72 1","pages":""},"PeriodicalIF":4.4000,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202401295","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
A concise and practical sustainable strategy for modular access to isoquinoline-fused benzo[f][1,3]oxazepine derivatives through a formal [4+3] annulation of commercially available salicyaldehydes with isoquinolinium salts has been developed. The reactions proceeded through the formation of two new bonds (C=C and C-O) and a seven-membered heterocyclic ring in one pot. Remarkably, use of simple NaHCO3 as a mild base, open atmosphere, nonhazardous reagents, nice functional group tolerance, and easily scale up are added characteristics to this approach. A wide range of substrates are compatible with this mild reaction system, thereby proving a facile and reliable protocol for constructing a benzo[f][1,3]oxazepine skeletons.
期刊介绍：
Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry.
The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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