1-Aminoethyl Substituted Chromanes 的规模化制备

IF 1.5 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Helvetica Chimica Acta Pub Date : 2023-11-03 DOI:10.1002/hlca.202300187

Stefan Diethelm, Gunther Schmidt, Thierry Sifferlen, Amandine Boller, Laurent Cornu, Christine Schmitt

{"title":"1-Aminoethyl Substituted Chromanes 的规模化制备","authors":"Stefan Diethelm, Gunther Schmidt, Thierry Sifferlen, Amandine Boller, Laurent Cornu, Christine Schmitt","doi":"10.1002/hlca.202300187","DOIUrl":null,"url":null,"abstract":"Chromanes and chromanones are structural motives found in many bioactive compounds. To support structure-activity-relationship (SAR) studies in a medicinal chemistry program, we developed two alternative synthetic strategies to access 1-aminoethyl chromane building blocks. Our strategies involve a C(sp2)−C(sp3) coupling for late-stage introduction of the aminoethyl side chain. In addition, an optimized process was developed to enable decagram scale preparation of one building block.","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 1","pages":""},"PeriodicalIF":1.5000,"publicationDate":"2023-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Scalable Preparation of 1-Aminoethyl Substituted Chromanes\",\"authors\":\"Stefan Diethelm, Gunther Schmidt, Thierry Sifferlen, Amandine Boller, Laurent Cornu, Christine Schmitt\",\"doi\":\"10.1002/hlca.202300187\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Chromanes and chromanones are structural motives found in many bioactive compounds. To support structure-activity-relationship (SAR) studies in a medicinal chemistry program, we developed two alternative synthetic strategies to access 1-aminoethyl chromane building blocks. Our strategies involve a C(sp2)−C(sp3) coupling for late-stage introduction of the aminoethyl side chain. In addition, an optimized process was developed to enable decagram scale preparation of one building block.\",\"PeriodicalId\":12842,\"journal\":{\"name\":\"Helvetica Chimica Acta\",\"volume\":\"107 1\",\"pages\":\"\"},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2023-11-03\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Helvetica Chimica Acta\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://onlinelibrary.wiley.com/doi/10.1002/hlca.202300187\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Helvetica Chimica Acta","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/hlca.202300187","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 0

摘要

铬烷和铬酮是许多生物活性化合物的结构基团。为了支持药物化学项目中的结构-活性-关系（SAR）研究，我们开发了两种可供选择的合成策略，以获得 1-氨基乙基色烷结构单元。我们的策略包括在后期引入氨基乙基侧链的 C(sp2)-C(sp3) 偶联。此外，我们还开发了一种优化工艺，可以十克规模制备一种构筑基块。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Scalable Preparation of 1-Aminoethyl Substituted Chromanes

Chromanes and chromanones are structural motives found in many bioactive compounds. To support structure-activity-relationship (SAR) studies in a medicinal chemistry program, we developed two alternative synthetic strategies to access 1-aminoethyl chromane building blocks. Our strategies involve a C(sp²)−C(sp³) coupling for late-stage introduction of the aminoethyl side chain. In addition, an optimized process was developed to enable decagram scale preparation of one building block.

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

Helvetica Chimica Acta 化学-化学综合

CiteScore

3.00

自引率

0.00%

发文量

审稿时长

2.3 months

期刊介绍： Helvetica Chimica Acta, founded by the Swiss Chemical Society in 1917, is a monthly multidisciplinary journal dedicated to the dissemination of knowledge in all disciplines of chemistry (organic, inorganic, physical, technical, theoretical and analytical chemistry) as well as research at the interface with other sciences, where molecular aspects are key to the findings. Helvetica Chimica Acta is committed to the publication of original, high quality papers at the frontier of scientific research. All contributions will be peer reviewed with the highest possible standards and published within 3 months of receipt, with no restriction on the length of the papers and in full color.