Qiushan Gao, Binbin Wang, Huanfeng Jiang and Wanqing Wu*,
{"title":"Palladium-Catalyzed Tandem Cyclization of Functional Diarylalkynes and Isocyanides for the Assembly of Isochromeno[4,3-c]quinolines","authors":"Qiushan Gao, Binbin Wang, Huanfeng Jiang and Wanqing Wu*, ","doi":"10.1021/acs.joc.4c0214210.1021/acs.joc.4c02142","DOIUrl":null,"url":null,"abstract":"<p >A novel strategy for the synthesis of various isochromeno[4,3-<i>c</i>]quinolines via palladium-catalyzed tandem cyclization of functional diarylalkynes with isocyanides has been developed. This approach features excellent chemo- and regioselectivities as well as good functional group tolerance. Notably, 6-phenylimino-6<i>H</i>-isochromeno[4,3-<i>c</i>]quinolin-11-amines and 11-amino-6<i>H</i>-isochromeno[4,3-<i>c</i>]quinolin-6-ones can be selectively constructed by employing different protecting groups of functional diarylalkynes. The gram-scale and late-stage modifications further demonstrate the synthetic value of this method.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"89 24","pages":"18370–18383 18370–18383"},"PeriodicalIF":3.3000,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.joc.4c02142","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A novel strategy for the synthesis of various isochromeno[4,3-c]quinolines via palladium-catalyzed tandem cyclization of functional diarylalkynes with isocyanides has been developed. This approach features excellent chemo- and regioselectivities as well as good functional group tolerance. Notably, 6-phenylimino-6H-isochromeno[4,3-c]quinolin-11-amines and 11-amino-6H-isochromeno[4,3-c]quinolin-6-ones can be selectively constructed by employing different protecting groups of functional diarylalkynes. The gram-scale and late-stage modifications further demonstrate the synthetic value of this method.
期刊介绍:
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.