Unprecedented Intramolecular Reactions of Heteroallene Salts for the Synthesis of Architecturally Diverse Nitrogen Heterocycles

有了这个新的奖项，化学合成计划支持佛蒙特州立农业学院大学的Matthias Brewer教授在一个项目中研究新的化学合成，该项目将为各种结构复杂的分子提供路线。其中一些新的转化将遵循目前合成方法无法实现的独特途径。将制备的新有机分子对于寻求开发新药物和其他生物学感兴趣分子的研究人员具有根本重要性。这些研究将为培养合成有机化学、反应设计、全合成和复杂结构解析领域的科学家提供一种机制。本项目还将为一名经济困难的高中生提供暑期研究经验。本项目将研究原位生成的1-氮杂-2-偶氮联烯盐在合成氮杂环中的分子内反应。这些新的杂丙二烯盐的方面，将探讨包括C-H插入反应，涉及氮杂吡啶离子中间体的反应，环加成反应和使用这种方法的全合成（+）-ibophyllidine。这项工作将为在温和、低温条件下制备结构复杂的氮杂环提供新的方法。

With this New award, the Chemical Synthesis Program supports Professor Matthias Brewer of University of Vermont & State Agricultural College in a project investigating new chemical syntheses that will provide routes to a variety of structurally complex molecules. Several of these new transformations will follow unique routes that are not accessible by current synthetic methods. The new organic molecules that will be prepared will be of fundamental importance to researchers seeking to develop new pharmaceuticals and other molecules of biological interest. These studies will provide a mechanism for the training of developing scientists in the areas of synthetic organic chemistry, reaction design, total synthesis and complex structure elucidation. This project will also give a summer research experience to an economically disadvantaged high school student.The project will investigate the intramolecular reactions of in situ-generated 1-aza-2-azoniaallene salts in the synthesis of nitrogen heterocycles. Aspects of these novel heteroallene salts that will be explored include C-H insertion reactions, reactions involving aziridinium ion intermediates, cycloaddition reactions and the use of this methodology for the total synthesis of (+)-ibophyllidine. This work will provide new ways to prepare structurally complex nitrogen heterocycles under mild, low temperature, conditions.