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

催化剂项目：利用二氢吡啶酮生成的吡咯合成新型杂芳族化合物

基本信息

批准号：
1956269
负责人：
Sezgin Kiren
金额：
$ 15万
依托单位：
Winston-Salem State University
依托单位国家：
美国
项目类别：
Standard Grant
财政年份：
2020
资助国家：
美国
起止时间：
2020-06-01 至 2024-05-31
项目状态：
已结题

来源：
https://www.nsf.gov/awardsearch/showAward?AWD_ID=1956269&HistoricalAwards=false
关键词：
Catalyst Project Synthesis Novel Heteroaromatic

项目摘要

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.

催化剂项目为历史悠久的黑人学院和大学提供支持，努力建立教师的研究能力，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师的研究能力，改善该机构的研究和教学。并让本科生参与研究经历。温斯顿塞勒姆州立大学的这个项目将研究新型化合物的有机合成。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得到应用。该研究将加强温斯顿塞勒姆州立大学本科生的研究，进一步提升该机构的研究能力。在这项研究中，将使用通过二氢吡啶与对甲苯磺酰甲基异氰化物（TosMIC）试剂反应获得的新型吡咯分子来开发新的方法和策略。由于这些未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，生成新型、复杂和稠合的杂芳族支架，其中包含吡咯、吡啶、吲哚、噻唑、中氮茚和嘧啶等特殊基序。酮的亲核加成、吡咯上的亲电芳族取代以及随后的氧化芳构化将使用简单的有机反应通过几个步骤产生结构独特的杂环。通过这些策略，将可以获得具有生物学意义的化合物喜树碱、异隐托平和替比法尼的类似物。该奖项反映了 NSF 的法定使命，并通过使用基金会的智力价值和更广泛的影响审查标准进行评估，被认为值得支持。