CAREER: New Methods for the Synthesis of Nitrogen-Containing Heterocycles

职业：含氮杂环合成新方法

• 批准号: 1845219
• 负责人: Michael Hilinski
• 金额: $ 67.5万
• 依托单位: University of Virginia Main Campus
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2019
• 资助国家: 美国
• 起止时间: 2019-04-15 至 2024-03-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1845219&HistoricalAwards=false
• 关键词: CAREER; New; Methods; Synthesis; Nitrogen

With this CAREER Award, the Chemical Synthesis Program of the NSF Division of Chemistry is supporting the research of Professor Michael Hilinski of the University of Virginia. Professor Hilinski is working with graduate and undergraduate students to develop new chemical reactions that allow for reductions in the cost, time, and waste associated with preparing chemical compounds. The targeted compounds have structural features that are found in the majority of Food and Drug Administration-approved drugs, as well as in other types of chemicals such as natural products, agricultural chemicals, and dyes. In addition to improving the ability to make known structures, the Hilinski laboratory is making structures that were previously unable to be made. This allows other scientists to explore potentially, societally-beneficial applications of these new compounds. The scientific approach being employed focuses on ways in which petroleum by-products react with other inexpensive chemicals to form ring structures containing at least one nitrogen atom. The use of catalysts to promote these reactions allows for predictable control of the products and for the synthesis of different ring sizes. The educational activities prepare students to communicate with non-scientists about their research and broader scientific implications. Professor Hilinski is creating and implementing a new science communication workshop for graduate and undergraduate students. He is also establishing a yearly Chemistry department open house event, and he is developing a new outreach activity for an audience of school-age children. Owing to the frequency with which nitrogen-containing heterocycles are found in pharmaceuticals, natural products, agrochemicals, and other bioactive or otherwise useful compounds, overcoming challenges in their synthesis is considered a key goal with broad potential impact. Professor Hilinski is developing new methods for saturated or partially saturated nitrogen-heterocycle synthesis that employ nitrenes as one-atom components in cycloaddition reactions. Several catalytic approaches are being pursued to achieve this underexploited strategy, including two-component formal cycloadditions initiated by nitrene transfer to olefins followed by spontaneous ring expansion or rearrangement, and multi-component formal cycloadditions between olefins, nitrenoid precursors, and a third component. Multiple classes of heterocycles of different ring sizes are being accessed using this strategy. The broader scientific impacts of this synthetic methodology research include the wide potential applicability to the synthesis of a variety of different compound classes. Other broader impacts include an enhancement students' skills in the area of science communication via establishment of a training workshop, and, through the education plan, the exposure of people in the local community to scientific research in a way that is accessible to a non-expert.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.

有了这个职业奖，NSF化学部的化学合成计划正在支持弗吉尼亚大学Michael Hilinski教授的研究。Hilinski教授正在与研究生和本科生合作开发新的化学反应，以减少与制备化合物相关的成本，时间和浪费。 目标化合物具有在大多数食品和药物管理局批准的药物中发现的结构特征，以及在其他类型的化学品中发现的结构特征，如天然产物，农用化学品和染料。除了提高制造已知结构的能力外，希林斯基实验室还在制造以前无法制造的结构。 这使得其他科学家能够探索这些新化合物的潜在社会有益应用。所采用的科学方法侧重于石油副产品与其他廉价化学品反应形成至少含有一个氮原子的环状结构的方式。使用催化剂来促进这些反应允许对产物的可预测的控制和不同环尺寸的合成。 这些教育活动使学生能够与非科学家交流他们的研究和更广泛的科学影响。教授Hilinski正在创建和实施一个新的研究生和本科生科学交流研讨会。 他还建立了每年一次的化学系开放日活动，他正在为学龄儿童观众开发一个新的外展活动。由于含氮杂环在药物、天然产物、农用化学品和其他生物活性或其他有用的化合物中发现的频率，克服其合成中的挑战被认为是具有广泛潜在影响的关键目标。Hilinski教授正在开发饱和或部分饱和氮杂环合成的新方法，该方法在环加成反应中使用氮烯作为单原子组分。几种催化方法正在寻求实现这一未充分开发的战略，包括两个组件的正式环加成引发的氮烯转移到烯烃，然后自发的环膨胀或重排，和烯烃，类氮烯前体，和第三个组件之间的多组分正式环加成。不同环大小的多个类别的杂环正在使用这种策略进行访问。这种合成方法研究的更广泛的科学影响包括对各种不同化合物类的合成的广泛潜在适用性。其他更广泛的影响包括通过建立培训讲习班，提高学生在科学传播领域的技能，并通过教育计划，当地社区的人们以一种非-该奖项反映了NSF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进行评估，被认为值得支持审查标准。