RUI: Reactions of 2-Aminopyrroles

氮杂环是一种重要的新药的来源，因此需要不断寻找新的途径。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-环系富含电子，在与贫电子氮二烯的反电子需求Diels-Alder反应中起到亲二烯的作用。将导致吡咯环环化为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氮酰亚胺的反应将导致有趣的杂环体系，其中一个吡咯环被环化成一个含有2个或3个氮原子的五元环--这些杂环化合物鲜为人知，具有潜在的生物活性，并且不容易通过其他方法获得。研究将确定1，3-偶极环加成反应是协同的还是分步的过程。有了这个奖项，有机和高分子化学计划支持宾夕法尼亚州立大学白兰地酒学院化学系的迈克尔·德·罗萨教授的研究。德·罗萨教授的研究工作主要集中在简单的2-氨基吡咯的化学上，而不会在环上进一步取代。首先由德罗莎教授的研究小组准备的化合物。以前的研究已经发现了几个新的2-氨基吡咯反应。建议的工作将导致新的反应途径，以获得有趣的，在某些情况下，以前未知的杂环系统。本科生将在暑期进行实验工作。预计该项目将支持10-12名本科生的工作。

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.