{"title":"靛红和 2-氯吡啶鎓盐的反应:α、β-不饱和羰基吲哚的高效和非对映选择性合成。","authors":"Kaveh Imani, Hamideh Shirazi, Golnaz Golchin, Ayoob Bazgir","doi":"10.1021/acs.joc.4c01069","DOIUrl":null,"url":null,"abstract":"<p><p>A new, mild, and diastereoselective method has been developed for the synthesis of β-pyridone-α,β-unsaturated oxindoles by the reaction of isatins and 2-chloropyridinium salts in EtOH at room temperature for 5 min. This method operates under mild reaction conditions, providing the product with a good yield and diastereoselectivity, and it exhibits excellent tolerance toward various functional groups. The predominant isomer is the <i>Z</i> isomer, which can convert to the <i>E</i> isomer in the presence of NaN<sub>3</sub>.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-09-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Reaction of Isatin and 2-Chloropyridinium Salt: An Efficient and Diastereoselective Synthesis of α,β-Unsaturated Oxindoles.\",\"authors\":\"Kaveh Imani, Hamideh Shirazi, Golnaz Golchin, Ayoob Bazgir\",\"doi\":\"10.1021/acs.joc.4c01069\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>A new, mild, and diastereoselective method has been developed for the synthesis of β-pyridone-α,β-unsaturated oxindoles by the reaction of isatins and 2-chloropyridinium salts in EtOH at room temperature for 5 min. This method operates under mild reaction conditions, providing the product with a good yield and diastereoselectivity, and it exhibits excellent tolerance toward various functional groups. The predominant isomer is the <i>Z</i> isomer, which can convert to the <i>E</i> isomer in the presence of NaN<sub>3</sub>.</p>\",\"PeriodicalId\":57,\"journal\":{\"name\":\"The Journal of Organic Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2024-09-22\",\"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://doi.org/10.1021/acs.joc.4c01069\",\"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://doi.org/10.1021/acs.joc.4c01069","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
摘要
本研究开发了一种新的、温和的非对映选择性方法,通过异汀和 2-氯吡啶鎓盐在 EtOH 中于室温下反应 5 分钟,合成 β-吡啶酮-α,β-不饱和吲哚。该方法反应条件温和,产物收率高且非对映选择性好,对各种官能团具有良好的耐受性。主要的异构体是 Z 异构体,在 NaN3 存在下可转化为 E 异构体。
Reaction of Isatin and 2-Chloropyridinium Salt: An Efficient and Diastereoselective Synthesis of α,β-Unsaturated Oxindoles.
A new, mild, and diastereoselective method has been developed for the synthesis of β-pyridone-α,β-unsaturated oxindoles by the reaction of isatins and 2-chloropyridinium salts in EtOH at room temperature for 5 min. This method operates under mild reaction conditions, providing the product with a good yield and diastereoselectivity, and it exhibits excellent tolerance toward various functional groups. The predominant isomer is the Z isomer, which can convert to the E isomer in the presence of NaN3.
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.