MsOH促进邻丙炔羟胺和醛合成4-芳基异恶唑烷和异恶唑烷

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-17 DOI:10.1021/acs.orglett.5c0138310.1021/acs.orglett.5c01383

Santosh J. Gharpure*, Kaushik C. Pansuriya and Juhi Pal,

{"title":"MsOH促进邻丙炔羟胺和醛合成4-芳基异恶唑烷和异恶唑烷","authors":"Santosh J. Gharpure*, Kaushik C. Pansuriya and Juhi Pal, ","doi":"10.1021/acs.orglett.5c0138310.1021/acs.orglett.5c01383","DOIUrl":null,"url":null,"abstract":"Temperature-dependent, Brønsted-acid-mediated divergent synthesis of 4-arylidene isoxazolidines and isoxazolines from O-propargyl hydroxylamines is developed. A series of control and crossover experiments have been carried out, revealing that the formation of 4-arylidene isoxazoline proceeds through an alkyne–oximium cyclization, ring-opening reaction, and subsequent condensation. Synthetic versatility of the developed methodology was highlighted in the synthesis of 3-aminoacrylaldehyde, β-hydroxy ketone, and isoxazole derivatives.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 21","pages":"5406–5411 5406–5411"},"PeriodicalIF":5.0000,"publicationDate":"2025-05-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"MsOH Promoted Divergent Synthesis of 4-Arylidene Isoxazolidines and Isoxazolines from O-Propargyl Hydroxylamines and Aldehydes\",\"authors\":\"Santosh J. Gharpure*, Kaushik C. Pansuriya and Juhi Pal, \",\"doi\":\"10.1021/acs.orglett.5c0138310.1021/acs.orglett.5c01383\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Temperature-dependent, Brønsted-acid-mediated divergent synthesis of 4-arylidene isoxazolidines and isoxazolines from O-propargyl hydroxylamines is developed. A series of control and crossover experiments have been carried out, revealing that the formation of 4-arylidene isoxazoline proceeds through an alkyne–oximium cyclization, ring-opening reaction, and subsequent condensation. Synthetic versatility of the developed methodology was highlighted in the synthesis of 3-aminoacrylaldehyde, β-hydroxy ketone, and isoxazole derivatives.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"27 21\",\"pages\":\"5406–5411 5406–5411\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-05-17\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.orglett.5c01383\",\"RegionNum\":1,\"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":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.orglett.5c01383","RegionNum":1,"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

以邻丙基羟胺为原料，建立了温度依赖、br / nsted酸介导的4-芳基异恶唑烷和异恶唑烷的发散合成。通过一系列的对照和交叉实验，揭示了4-芳基异恶唑啉的生成是经过炔-肟环化、开环和缩合反应的。该方法在合成3-氨基丙烯醛、β-羟基酮和异恶唑衍生物方面的通用性突出。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

MsOH Promoted Divergent Synthesis of 4-Arylidene Isoxazolidines and Isoxazolines from O-Propargyl Hydroxylamines and Aldehydes

查看原文本刊更多论文

MsOH Promoted Divergent Synthesis of 4-Arylidene Isoxazolidines and Isoxazolines from O-Propargyl Hydroxylamines and Aldehydes

Temperature-dependent, Brønsted-acid-mediated divergent synthesis of 4-arylidene isoxazolidines and isoxazolines from O-propargyl hydroxylamines is developed. A series of control and crossover experiments have been carried out, revealing that the formation of 4-arylidene isoxazoline proceeds through an alkyne–oximium cyclization, ring-opening reaction, and subsequent condensation. Synthetic versatility of the developed methodology was highlighted in the synthesis of 3-aminoacrylaldehyde, β-hydroxy ketone, and isoxazole derivatives.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.