{"title":"6π 1,5-二氮杂环化伊沙廷、α-酮甾烷衍生肼与α,β-不饱和酮甾烷、酮和醛实现功能化吡唑","authors":"Liu Song*, and , Mi Zhou, ","doi":"10.1021/acs.joc.4c0207010.1021/acs.joc.4c02070","DOIUrl":null,"url":null,"abstract":"<p >A novel and efficient 6π 1,5-diaza-electrocyclization of readily available isatin, α-ketoester derived hydrazones with α,β-unsaturated ketoesters, ketones, and aldehydes has been developed. A series of functionalized pyrazoles bearing an oxindole unit were easily afforded by this tool with good yields and high functional group tolerance under mild conditions. Importantly, the obtained pyrazole could be further converted to 3-pyrazolecarboxylic acid with a quaternary carbon stereocenter.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16952–16956 16952–16956"},"PeriodicalIF":3.3000,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"6π 1,5-Diaza-electrocyclization of Isatin, α-Ketoester Derived Hydrazones with α,β-Unsaturated Ketoesters, Ketones, and Aldehydes Enables Functionalized Pyrazoles\",\"authors\":\"Liu Song*, and , Mi Zhou, \",\"doi\":\"10.1021/acs.joc.4c0207010.1021/acs.joc.4c02070\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >A novel and efficient 6π 1,5-diaza-electrocyclization of readily available isatin, α-ketoester derived hydrazones with α,β-unsaturated ketoesters, ketones, and aldehydes has been developed. A series of functionalized pyrazoles bearing an oxindole unit were easily afforded by this tool with good yields and high functional group tolerance under mild conditions. Importantly, the obtained pyrazole could be further converted to 3-pyrazolecarboxylic acid with a quaternary carbon stereocenter.</p>\",\"PeriodicalId\":57,\"journal\":{\"name\":\"The Journal of Organic Chemistry\",\"volume\":\"89 22\",\"pages\":\"16952–16956 16952–16956\"},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2024-11-05\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"The Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.joc.4c02070\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.joc.4c02070","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
6π 1,5-Diaza-electrocyclization of Isatin, α-Ketoester Derived Hydrazones with α,β-Unsaturated Ketoesters, Ketones, and Aldehydes Enables Functionalized Pyrazoles
A novel and efficient 6π 1,5-diaza-electrocyclization of readily available isatin, α-ketoester derived hydrazones with α,β-unsaturated ketoesters, ketones, and aldehydes has been developed. A series of functionalized pyrazoles bearing an oxindole unit were easily afforded by this tool with good yields and high functional group tolerance under mild conditions. Importantly, the obtained pyrazole could be further converted to 3-pyrazolecarboxylic acid with a quaternary carbon stereocenter.
期刊介绍:
The 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.