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大学和州立农业学院的马蒂亚斯·布鲁尔教授研究新的化学合成，这将为各种结构复杂的分子提供路线。其中几个新的转变将遵循目前的合成方法无法达到的独特路线。即将制备的新有机分子将对寻求开发新药物和其他生物感兴趣的分子的研究人员具有根本性的重要性。这些研究将为在合成有机化学、反应设计、全合成和复杂结构阐明方面培训发展中的科学家提供一种机制。该项目还将为一名经济困难的高中生提供暑期研究经验。该项目将研究原位生成的1-氮杂-2-偶氮烯盐在合成氮杂环过程中的分子内反应。这些新型的杂烯类盐将被探索的方面包括C-H插入反应、涉及氮杂环丙烷离子中间体的反应、环加成反应以及使用该方法全合成(+)-ibophyllidine。这项工作将为在温和的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.