RUI: Synthesis of Highly Functionalized N-Alkyl 2-Pyridones and Their Analogues

RUI：高功能化N-烷基2-吡啶酮及其类似物的合成

• 批准号: 1266314
• 负责人: Carolyn Anderson
• 金额: $ 23万
• 依托单位: Calvin University
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2013
• 资助国家: 美国
• 起止时间: 2013-05-15 至 2017-04-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1266314&HistoricalAwards=false
• 关键词: RUI; Synthesis; Highly; Functionalized; Alkyl

In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Carolyn Anderson of the Department of Chemistry and Biochemistry at Calvin College will explore the development of facile methods for the synthesis of structures containing N-alkyl pyridones and their further transformation into targets of importance. These targets include a unique class of amino acid homologues, which will subsequently be used to expand our understanding of the helical structure of peptides containing these subunits. The development of asymmetric variants of these methods will also be pursued. These methods are based on the conversion of readily available 2-alkoxypyridine substrates. This work could lead to a suite of chiral and achiral methods for preparing highly functionalized N-alkyl 2-pyridones. Such chemistry will make these and their related analogues available to the broader chemical community. In addition, basic knowledge related to asymmetric gold(III) catalysis is also expected to be garnered during these studies. Successful development of these methodologies and targets will have an impact on the synthetic community as well as those involved in the development of organic materials, medicinal leads, and asymmetric transformations. In addition, these efforts will provide excellent training for undergraduate research collaborators and an opportunity for pre-college students, especially those from historically underrepresented groups, to gain hands-on experience in the chemistry laboratory.

在这个由化学系化学合成计划资助的项目中，卡尔文学院化学与生物化学系的Carolyn安德森教授将探索合成含N-烷基吡啶酮结构的简便方法的发展，以及将其进一步转化为重要目标。这些目标包括一类独特的氨基酸同源物，随后将用于扩展我们对含有这些亚基的肽的螺旋结构的理解。这些方法的不对称变体的开发也将继续进行。 这些方法基于容易获得的2-烷氧基吡啶底物的转化。 本工作为制备高功能化的N-烷基-2-吡啶酮提供了一套手性和非手性的合成方法。这种化学方法将使这些化合物及其相关类似物可供更广泛的化学界使用。此外，与不对称金（III）催化相关的基本知识也有望在这些研究中获得。这些方法和目标的成功开发将对合成社区以及参与有机材料，药用铅和不对称转化的开发的人产生影响。此外，这些努力将为本科研究合作者提供良好的培训，并为大学预科学生，特别是那些来自历史上代表性不足的群体的学生提供机会，以获得化学实验室的实践经验。

项目成果

Correction to Synthesis of N -Alkenyl 2-Pyridonyl Ethers via a Au(I)-Catalyzed Rearrangement of 2-Propargyloxypyridines

通过 Au(I) 催化 2-炔丙氧基吡啶重排校正 N-烯基 2-吡啶酮醚的合成

• DOI: 10.1021/acs.joc.0c00151
• 发表时间: 2020
• 期刊: The Journal of Organic Chemistry
• 作者: Romero, Evan O.;Reidy, Connor P.;Bootsma, Andrea N.;PreFontaine, Noah M.;Vryhof, Nicholas W.;Wierenga, David C.;Anderson, Carolyn E.
• 通讯作者: Anderson, Carolyn E.