Catalyst Project: Synthesis of Novel Heteroaromatic Compounds Using Pyrroles Generated from Dihydropyridones

Catalyst项目为历史上的黑人学院和大学提供支持，以建立教师的研究能力，加强科学、技术、工程和数学本科教育和研究。预计该奖项将进一步提高该教员的研究能力，提高该机构的研究和教学水平。让本科生参与研究体验。温斯顿塞勒姆州立大学的这个项目将研究新化合物的有机合成。了解如何合成这些化合物将在材料科学、药物化学和其他领域有应用。这项研究将加强温斯顿塞勒姆州立大学本科生的研究，并进一步提高该机构的研究能力。本研究将利用二氢吡啶与对甲苯磺酰基甲基异氰酸酯（TosMIC）试剂反应得到的新型吡咯分子，开发新的方法和策略。由于这些未被充分利用的分子具有吡咯、酮和胺等功能，它们将进一步被功能化，以产生具有吡咯、吡啶、吲哚、噻唑、吲哚和嘧啶等特殊基序的新型、复杂和融合的杂芳香支架。在酮上亲核加成，在吡咯上亲电芳香取代，然后进行氧化芳构化，通过简单的有机反应，只需几个步骤就能得到结构独特的杂环。有了这些策略，具有重要生物学意义的化合物Camphthothein、Isocryptolepine和Tibifarnib的类似物就可以获得。该奖项反映了美国国家科学基金会的法定使命，并通过使用基金会的知识价值和更广泛的影响审查标准进行评估，被认为值得支持。

Catalyst Projects provide support for Historically Black Colleges and Universities to work towards establishing research capacity of faculty to strengthen science, technology, engineering and mathematics undergraduate education and research. It is expected that the award will further the faculty member's research capability, improve research and teaching at the institution. and involve undergraduate students in research experiences. This project at Winston Salem State University will study the organic synthesis of novel compounds. Understanding how to synthesize these compounds will have applications in materials science, pharmaceutical chemistry and other fields. The research will enhance undergraduate student research at Winston Salem State University and further enhance the research capabilities of the institution. In this research, new methodologies and strategies will be developed using the novel pyrrole molecules that will be obtained from the reaction of dihydropyridines with p-toluenesulfonylmethyl isocyanide (TosMIC) reagent. As these underutilized molecules possess such functionalities as pyrrole, ketone and amine, they will further be functionalized to generate novel, complex and fused heteroaromatic scaffolds hosting such privileged motifs as pyrrole, pyridine, indole, thiazoles, indolizines and pyrimidines. Nucleophilic additions to the ketone, electrophilic aromatic substitutions on the pyrrole followed by oxidative aromatization will lead to structurally unique heterocycles in a couple of steps using simple organic reactions. With these strategies, analogs of biologically significant compounds Camphthothein, Isocryptolepine and Tibifarnib will be accessible.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.