RUI: Reactions of 2-Aminopyrroles

RUI：2-氨基吡咯的反应

• 批准号: 0910668
• 负责人: Michael De Rosa
• 金额: $ 17.7万
• 依托单位: Pennsylvania State Univ University Park
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2009
• 资助国家: 美国
• 起止时间: 2009-08-01 至 2013-07-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=0910668&HistoricalAwards=false
• 关键词: RUI; Reactions; Aminopyrroles

There exists a continuing need for new routes to nitrogen heterocycles--a source of important new drugs. This project continues support for the study of 2-aminopyrroles as precursors for novel nitrogen heterocycles. The 2-aminopyrrole-ring system is electron rich and can act as a dienophile in inverse-electron demand Diels-Alder reactions with electron poor azadienes. Reactions that will lead to a pyrrole ring annulated to a six-membered ring containing one or two nitrogen atoms. The 1,3-dipolar cycloaddition reaction of 2-aminopyrroles has never been reported. Reactions of 2-aminopyrroles with phenyl azides and nitrilimines would lead to interesting heterocyclic systems in which a pyrrole ring is annulated to a five-membered ring containing 2 or 3 nitrogen atoms--heterocyclic compounds that are poorly known, with potential biological activity, and not readily available by other methods. Studies will be carried out to determine if the 1,3-dipolar cycloaddition reaction is concerted or a step-wise process.With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Michael De Rosa of the Department of Chemistry at Penn State Brandywine. Professor De Rosa's research efforts focus on the chemistry of simple 2-aminopyrroles without further substitution on the ring. Compounds first prepared in Professor De Rosa's research group. Previous studies have discovered several new reactions of 2-aminopyrroles. The proposed work should lead to novel reaction pathways to interesting, and in some cases, previously unknown heterocyclic systems. Undergraduates will carry out experimental work during the summer. It is expected that this project will support the work of 10-12 undergraduates.

对氮杂环的新途径的需求持续存在，氮杂环是重要新药的来源。该项目继续支持2-氨基吡咯作为新型氮杂环前体的研究。2-氨基吡咯环系统是富电子的，在与缺电子偶氮杂烯的反电子需求Diels-Alder反应中可以作为亲二酚。将吡咯环环化成含有一个或两个氮原子的六元环的反应。2-氨基吡咯的1,3-偶极环加成反应尚未见报道。2-氨基吡咯与苯基叠氮化物和硝基胺的反应会产生有趣的杂环体系，其中一个吡咯环被环成一个含有2或3个氮原子的五元环——这是一种鲜为人知的杂环化合物，具有潜在的生物活性，并且不易通过其他方法获得。研究将进行，以确定是否1,3-偶极环加成反应是协调或逐步过程。有了这个奖项，有机和大分子化学项目支持宾夕法尼亚州立大学白兰地酒学院化学系迈克尔·德·罗莎教授的研究。De Rosa教授的研究重点是在环上没有进一步取代的简单2-氨基吡咯的化学反应。这些化合物最初是由德罗萨教授的研究小组制备的。以前的研究已经发现了几种新的2-氨基吡咯反应。提出的工作应该导致新的反应途径有趣，在某些情况下，以前未知的杂环系统。本科生将在夏季进行实验工作。预计该项目将支持10-12名本科生的工作。