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

催化剂项目支持历史悠久的黑人学院和大学致力于建立教职员工的研究能力，以加强科学、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教职员工的研究能力，改善该机构的研究和教学。并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、药物化学等领域得到应用。这项研究将加强温斯顿·塞勒姆州立大学的本科生研究，并进一步增强该机构的研究能力。在这项研究中，将利用二氢吡啶与对甲苯磺酰甲基异氰酸酯(TosMIC)试剂反应得到的新型吡咯分子来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、酮和胺等官能团，它们将被进一步功能化，以生成具有吡咯、吡啶、吲哚、噻唑、吲哚和嘧啶等特权基元的新型、复杂和稠合的杂芳族支架。酮的亲核加成、吡咯上的亲电芳香族取代以及氧化芳构化将通过几步简单的有机反应得到结构独特的杂环化合物。通过这些策略，将可以获得具有生物学意义的化合物樟脑素、异托品和替比巴尼的类似物。这一奖项反映了NSF的法定使命，并通过使用基金会的智力优势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.