{"title":"通过区域选择性氧化腈环加成和原位消除,从β-亚磺酰基和β-磺酰基环己烯酮简便合成异噁唑的路线","authors":"","doi":"10.1016/j.tetlet.2024.155316","DOIUrl":null,"url":null,"abstract":"<div><div>A facile synthetic route to isoxazole is reported. Through examination of the reaction of stable nitrile oxides, β-substituted cyclohexenones, particularly sulfinyl and sulfonyl derivatives, show excellent regioselectivity in the 1,3-dipolar cycloaddition, forming isoxazoline cycloadducts, which undergo in-situ 1,2-elimination either with the assistance of a base (for the β-sulfonyl derivative) or without the need for a base (for the β-sulfinyl derivative), enabling a direct, high-yield access to isoxazoles.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":null,"pages":null},"PeriodicalIF":1.5000,"publicationDate":"2024-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Facile synthetic route to isoxazoles from β-sulfinyl- and β-sulfonyl-cyclohexenones via regioselective nitrile oxide cycloaddition and in-situ elimination\",\"authors\":\"\",\"doi\":\"10.1016/j.tetlet.2024.155316\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A facile synthetic route to isoxazole is reported. Through examination of the reaction of stable nitrile oxides, β-substituted cyclohexenones, particularly sulfinyl and sulfonyl derivatives, show excellent regioselectivity in the 1,3-dipolar cycloaddition, forming isoxazoline cycloadducts, which undergo in-situ 1,2-elimination either with the assistance of a base (for the β-sulfonyl derivative) or without the need for a base (for the β-sulfinyl derivative), enabling a direct, high-yield access to isoxazoles.</div></div>\",\"PeriodicalId\":438,\"journal\":{\"name\":\"Tetrahedron Letters\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2024-09-29\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040403924004118\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403924004118","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Facile synthetic route to isoxazoles from β-sulfinyl- and β-sulfonyl-cyclohexenones via regioselective nitrile oxide cycloaddition and in-situ elimination
A facile synthetic route to isoxazole is reported. Through examination of the reaction of stable nitrile oxides, β-substituted cyclohexenones, particularly sulfinyl and sulfonyl derivatives, show excellent regioselectivity in the 1,3-dipolar cycloaddition, forming isoxazoline cycloadducts, which undergo in-situ 1,2-elimination either with the assistance of a base (for the β-sulfonyl derivative) or without the need for a base (for the β-sulfinyl derivative), enabling a direct, high-yield access to isoxazoles.
期刊介绍:
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.