RUI: Reactions of Aminopyrroles

美国国家科学基金会化学部的化学合成项目支持宾夕法尼亚州立大学化学系Michael De Rosa教授的项目。De Rosa教授研究氨基吡咯一类特殊化合物的合成和化学反应。这些分子由一个碳原子环和两个氮原子组成，一个在五元环内，另一个作为取代基附着在环上。德·罗萨教授使用氨基吡咯来合成包含两个或三个环的更复杂的分子。这些新的反应在有机化学中是重要的，因为它们使简单分子有效和选择性地转化为更复杂的三维分子。许多具有生物活性的分子和药物具有类似于这些反应形成的三维结构。更广泛地说，有机化学的发展推动了生物、医学和材料领域的发展，同时也促进了经济发展和环境的可持续性。大学生科研训练在学生成长为科学家的过程中起着不可或缺的作用。De Rosa教授在这个项目中与本科生一起工作，并为他们继续接受四年制化学学位课程和其他课程的培训做好准备。氨基吡咯是由De Rosa教授和他的学生同事首次制备的富电子物质。由于其新颖的电子结构，氨基吡咯在与偶氮杂烯的反电子需求Diels-Alder （IEDDA）环加成反应中扮演亲二酚的角色。因此，从简单易得的氨基吡咯快速制备复杂的杂环体系，收率高，有机废物少。这些反应产生新的杂环，用目前的方法是不容易制备的。这种化学为复杂的杂环系统提供了新的无金属途径，这是绿色化学的一个目标。氨基吡咯在多组分反应中应用的可能性也在探索中。这个研究项目是与本科生合作进行的，为他们提供宝贵的经验，以加强他们的职业准备。

The Chemical Synthesis Program of the NSF Chemistry Division supports the project by Professor Michael De Rosa in the Department of Chemistry at Penn State-Brandywine. Professor De Rosa studies the synthesis and chemical reactions of a particular class of compounds called aminopyrroles. These molecules are comprised of a ring of carbon atoms with two nitrogen atoms, one within a five-membered ring and one attached as a substituent to the ring. Professor De Rosa uses aminopyrroles are to synthesize more complex molecules that contain two or three rings. These new reactions are important in organic chemistry because they enable efficient and selective transformation of simple molecules to three-dimensional molecules of greater complexity. Many biologically active molecules and pharmaceuticals have three-dimensional structures similar to those constructed by these reactions. More generally, developments in organic chemistry advance the fields of biology, medicine, and materials, as well as promoting economic development and environmental sustainability. Undergraduate student research training performs an indispensable role in the growth of students into scientists. Professor De Rosa works with undergraduate students in this project and prepares them to continue their training in four-year chemistry degree programs and beyond.Aminopyrroles are electron rich substances that were prepared for the first time by Professor De Rosa and his student coworkers. As a consequence of their novel electronic structure, aminopyrroles act as dienophiles in inverse-electron demand Diels-Alder (IEDDA) cycloaddition reactions with azines (azadienes). Complex heterocyclic ring systems are thus rapidly prepared from simple readily available aminopyrroles in good yield and with minimal organic waste. These reactions yield novel heterocycles that are not readily prepared using current methods. This chemistry provides new metal free routes to complex heterocyclic systems, a goal of green chemistry. The possibility that aminopyrroles can be used in multicomponent reactions also is being explored. This research project is carried out in collaboration with undergraduate students, providing valuable experience to enhance their career preparation.