New Organic and Organometallic Synthetic Methods for Manipulation of Pyridine and Related Azole Anhydrobases

在这项由化学系化学合成计划资助的项目中，爱荷华大学化学系教授Christopher Pigge将研究通过操纵亚烷基二氢吡啶(无氢碱)和相关中间体来构建氮杂杂环体系的新方法。虽然无氢碱是公认的化合物，但它们作为合成中间体的用途还没有得到广泛的探索。在这个项目中，将开发传统的成键方法以及有机过渡金属催化的过程(例如，钯、铑、金)，以利用吡啶和相关的氮杂杂环无氢碱的合成潜力。还将开展不对称金属催化转化的研究。这项工作可以为各种含氮杂环体系的普遍制备提供更有效的方法。这些类型的化合物普遍存在于具有生物活性的天然产品和药品中。此外，氮杂杂环衍生物也是有机发光二极管和有机半导体等功能材料的常见构件。因此，该项目的成功实施将对从有机合成、药物化学到材料研究等众多当代重要化学研究领域产生影响。此外，该项目将为本科生和研究生提供极好的培训，包括那些在科学界历来代表性不足的学生。

In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Christopher Pigge of the Department of Chemistry at the University of Iowa will investigate new approaches to construct aza-heterocyclic ring systems via manipulation of alkylidene dihydropyridines (anhydrobases) and related intermediates. While anhydrobases are established compounds, their use as synthetic intermediates has not been extensively explored. In this project both conventional bond forming methods as well as organotransition metal-catalyzed processes (e.g., palladium, rhodium, gold) will be developed in order to harness the synthetic potential of pyridine and related aza-heterocyclic anhydrobases. Development of asymmetric metal-catalyzed transformations also will be undertaken. This work could lead to more efficient methods for the general preparation of various nitrogen-containing heterocyclic ring systems. These types of compounds are ubiquitous in biologically active natural products and pharmaceuticals. Moreover, aza-heterocyclic derivatives are also common building blocks of functional materials such as organic light emitting diodes and organic semiconductors. Thus, successful execution of this project will impact numerous fields of important contemporary chemical research in areas ranging from organic synthesis and medicinal chemistry to materials research. In addition, this project will provide excellent training of undergraduate and graduate students, including those from groups historically underrepresented in the sciences.