温和条件下涉及香豆素-3-甲酰基吡唑的意想不到的迈克尔式加成-去酰基吡唑

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2024-11-08 DOI:10.1016/j.tet.2024.134360

Chuan-Wen Lei , Jiao-Jiao Lei , Xiao-Li Feng , Wen-Hui Zhang , Ze-Gang Ma , You-Ping Tian , Ying Zhou

{"title":"温和条件下涉及香豆素-3-甲酰基吡唑的意想不到的迈克尔式加成-去酰基吡唑","authors":"Chuan-Wen Lei , Jiao-Jiao Lei , Xiao-Li Feng , Wen-Hui Zhang , Ze-Gang Ma , You-Ping Tian , Ying Zhou","doi":"10.1016/j.tet.2024.134360","DOIUrl":null,"url":null,"abstract":"<div><div>The first Michael type addition-deacylpyrazole involving α,β-unsaturated pyrazolamides was accomplished by utilizing DMAP as catalyst in mild condition. The protocol enables the access to various oxindole-substituted dihydrocoumarins from coumarin-3-formylpyrazoles and 3-acetoxy oxindoles in excellent yields (up to 99 % yield) with acceptable diastereoselectivities (up to >95:5 dr). In this work, the acylpyrazole group of coumarin-3-formylpyrazoles acted as a temporary activating group for the first time. Detailed mechanistic studies were performed with high resolution mass spectrometry (HRMS) analysis.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134360"},"PeriodicalIF":2.1000,"publicationDate":"2024-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"An unexpected Michael type addition-deacylpyrazole involving coumarin-3-formylpyrazoles under mild conditions\",\"authors\":\"Chuan-Wen Lei , Jiao-Jiao Lei , Xiao-Li Feng , Wen-Hui Zhang , Ze-Gang Ma , You-Ping Tian , Ying Zhou\",\"doi\":\"10.1016/j.tet.2024.134360\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>The first Michael type addition-deacylpyrazole involving α,β-unsaturated pyrazolamides was accomplished by utilizing DMAP as catalyst in mild condition. The protocol enables the access to various oxindole-substituted dihydrocoumarins from coumarin-3-formylpyrazoles and 3-acetoxy oxindoles in excellent yields (up to 99 % yield) with acceptable diastereoselectivities (up to >95:5 dr). In this work, the acylpyrazole group of coumarin-3-formylpyrazoles acted as a temporary activating group for the first time. Detailed mechanistic studies were performed with high resolution mass spectrometry (HRMS) analysis.</div></div>\",\"PeriodicalId\":437,\"journal\":{\"name\":\"Tetrahedron\",\"volume\":\"169 \",\"pages\":\"Article 134360\"},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2024-11-08\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040402024005416\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402024005416","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

利用 DMAP 作为催化剂，在温和条件下首次完成了涉及 α、β-不饱和吡唑酰胺的迈克尔加成-去乙酰基吡唑。该方法可以从香豆素-3-甲酰基吡唑和 3-乙酰氧基氧茚酮中获得各种吲哚取代的二氢香豆素，收率极高（高达 99%），非对映选择性也可以接受（高达 95:5dr）。在这项工作中，香豆素-3-甲酰基吡唑的酰基吡唑基团首次充当了临时活化基团。通过高分辨率质谱分析进行了详细的机理研究。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

An unexpected Michael type addition-deacylpyrazole involving coumarin-3-formylpyrazoles under mild conditions

查看原文本刊更多论文

An unexpected Michael type addition-deacylpyrazole involving coumarin-3-formylpyrazoles under mild conditions

The first Michael type addition-deacylpyrazole involving α,β-unsaturated pyrazolamides was accomplished by utilizing DMAP as catalyst in mild condition. The protocol enables the access to various oxindole-substituted dihydrocoumarins from coumarin-3-formylpyrazoles and 3-acetoxy oxindoles in excellent yields (up to 99 % yield) with acceptable diastereoselectivities (up to >95:5 dr). In this work, the acylpyrazole group of coumarin-3-formylpyrazoles acted as a temporary activating group for the first time. Detailed mechanistic studies were performed with high resolution mass spectrometry (HRMS) analysis.

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

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.