Dehydration of carboxylic acids and tertiary amides promoted by sulfonium salts for ketene and ketene iminium generation and cycloaddition

锍盐促进的羧酸和叔酰胺脱水，用于烯酮和烯酮亚胺的生成和环加成

基本信息

批准号：
537546-2018
负责人：
Bélanger, Guillaume
金额：
$ 1.82万
依托单位：
Université de Sherbrooke
依托单位国家：
加拿大
项目类别：
Engage Grants Program
财政年份：
2018
资助国家：
加拿大
起止时间：
2018-01-01 至 2019-12-31
项目状态：
已结题

来源：
https://www.nserc-crsng.gc.ca/ase-oro/Details-Detailles_eng.asp?id=645015
关键词：
Dehydration carboxylic acids tertiary amides

项目摘要

OmegaChem has developed two fields of expertise over the years, namely in the development of new, stable reagents (principally sulfonium salts) and in the research in medicinal chemistry (contract-based). The company is now seeking other applications that will a) open new avenues, b) be of general interest to organic chemists, and c) ideally serve their second field of expertise, namely the preparation of functionalized polycyclic frameworks toward biologically relevant classes of drugs. Ketenes are particularly appealing in this context: they are prepared by dehydration of carboxylic acids or derivatives and, upon intramolecular cycloaddition, generate varied bicyclic ketones, thus addressing all objectives. In this proposal, we want to develop a mild, low temperature dehydration of carboxylic acids and amides using sulfonium salts to generate ketenes and ketene iminiums ions that will be trapped in situ with an internal alkene or alkyne. Ring size, functional group compatibility as well as substitution on the substrate will be studied. Not only may we develop new sulfonium salts to be included in the arsenal of reagents proposed by OmegaChem, we will also develop new chemistry accessible with such reagents. This project is part of OmegaChem development strategy to advance their expertise and further affirm their unique international leadership as Canadian experts in specialized sulfonium reagents for dehydrative transformations.**

多年来，Omegachem已开发了两个专业知识领域，即开发新的稳定试剂（主要是硫盐）和药物化学研究（基于合同）的研究。该公司现在正在寻求其他将a）开放新途径的应用程序，b）有机化学家普遍兴趣，c）理想地服务于第二个专业知识领域，即准备官能化的多环形框架用于生物学相关的药物类别。在这种情况下，酮特别有吸引力：它们是通过羧酸或衍生物的脱水来制备的，并且在分子内环载条件下产生各种的双环酮，从而解决所有目标。在此提案中，我们希望使用硫酸盐和酰胺的羧酸和酰胺的温度低温脱水，以产生酮和酮胺离子，并将其原位与内部烷烃或炔烃一起捕获。将研究环大小，功能组兼容性以及基板上的替代。我们不仅可以开发出新的硫盐盐将包含在Omegachem提出的试剂库中，而且我们还将开发可与此类试剂一起使用的新化学物质。该项目是Omegachem开发战略的一部分，旨在提高其专业知识，并进一步确认其独特的国际领导地位，是加拿大专业磺基试剂专家的脱水转型。**