New Reaction Cascades for Organic Synthesis

有机合成的新级联反应

基本信息

批准号：
1855708
负责人：
Jon Njardarson
金额：
$ 48.5万
依托单位：
University of Arizona
依托单位国家：
美国
项目类别：
Standard Grant
财政年份：
2019
资助国家：
美国
起止时间：
2019-09-01 至 2022-09-30
项目状态：
已结题

来源：
https://www.nsf.gov/awardsearch/showAward?AWD_ID=1855708&HistoricalAwards=false
关键词：
New Reaction Cascades Organic Synthesis

项目摘要

With this award, the Chemical Synthesis Program of the NSF Division of Chemistry is supporting the research of Professor Jon T. Njardarson in the Department of Chemistry and Biochemistry at The University of Arizona. Professor Njardarson is working with a group of graduate and undergraduate students on making novel organic molecules that may benefit the pharmaceutical, flavors, fragrance, agrochemicals industries. Specifically, Professor Njardarson and his team of students are developing powerful new methods of chemical synthesis leading to high value molecular target structures. Flat carbon-containing rings (aromatics) and chiral molecules (compounds that have specific 3-dimentional structures) are indispensable chemical industry building blocks. This research is focused on developing new reactions for making both aromatic and chiral molecules. The educational deliverables of this project include the participation of graduate and undergraduate students in hands-on research. Professor Njardarson and his group put together visually beautiful teaching tools such as free mobile applications (app) and websites entitled Chemistry By Design, posters of the Top 200 pharmaceuticals, and Disease and Structure posters of drug targets. These educational tools provide the public with new opportunities to learn about organic chemistry and its importance to society. Professor Njardarson and his students design and develop new chemical reactions for the assembly of important molecular building blocks such as aromatic and chiral structures using innovative approaches. A reaction cascade in organic chemistry is a process in which multiple reactions take place consecutively (in tandem) in a reaction flask. Cascade reactions represent a powerful platform for streamlining synthesis by allowing multiple bonds to be forged in one pot, resulting in high-value structural output. Using simple chemical building blocks, Professor Njardarson demonstrates that structurally complex aromatic and chiral structures can be assembled using novel anionic or catalyst mediated reaction cascades. These new reaction cascades are tunable and can be diverted in a multitude of ways to provide access to a diverse array of important organic building blocks. This research is focused on elucidating and understanding the detailed reaction mechanisms of these cascades, so that the resulting knowledge foundation can be of broad use and value. Broader impacts include the useful new chemical reactions that are expected to find use in industry and academia. Furthermore, the suite of novel chemical education products such as the Top 200 chemical target posters and the app "Chemistry By Design" are used in instruction around the world.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.

通过该奖项，NSF化学部的化学综合计划支持乔恩·T·Njardarson教授在亚利桑那大学化学和生物化学系的研究。 Njardarson教授正在与一群研究生和本科生合作制作新颖的有机分子，这些分子可能受益于药物，口味，香水，农业化学行业。具体来说，Njardarson教授及其学生团队正在开发强大的化学合成方法，从而导致高价值的分子目标结构。含碳的平坦环（芳香剂）和手性分子（具有特定三维结构的化合物）是必不可少的化学工业基础。这项研究的重点是开发新反应，以制作芳香和手性分子。该项目的教育可交付成果包括研究生和本科生的动手研究。 Njardarson教授及其小组将视觉上美丽的教学工具汇总在一起，例如免费移动应用程序（APP）和网站，名为“通过设计，前200名药品的海报以及药物目标的疾病和结构海报”的网站。这些教育工具为公众提供了了解有机化学及其对社会重要性的新机会。 Njardarson教授及其学生使用创新方法来设计和开发新的化学反应，以组装重要的分子构建块，例如芳香和手性结构。有机化学中的反应级联反应是一个过程，在该过程中，在反应瓶中连续（同时）进行多种反应。级联反应代表了一个强大的平台，可以通过在一个锅中锻造多个键来简化合成，从而导致高价值的结构输出。使用简单的化学构建块，Njardarson教授表明，可以使用新型阴离子或催化剂介导的反应级联反应级联组装结构复杂的芳香族和手性结构。这些新的反应级联反应是可调的，可以通过多种方式进行转移，以提供访问各种重要的有机构建块。这项研究的重点是阐明和理解这些级联的详细反应机制，因此所产生的知识基础可以广泛使用和价值。更广泛的影响包括有用的新化学反应，预计将在行业和学术界找到使用。此外，在世界各地的指导中使用了新型化学教育产品的套件，例如前200个化学目标海报和应用程序“化学”。该奖项反映了NSF的法定任务，并被认为值得通过基金会的知识分子优点和更广泛的影响审查标准通过评估来进行评估。

项目成果

期刊论文数量（8）

专著数量（0）

科研奖励数量（0）

会议论文数量（0）

专利数量（0）

A Structural Analysis of the FDA Green Book-Approved Veterinary Drugs and Roles in Human Medicine

DOI：
10.1021/acs.jmedchem.0c01502
发表时间：
2020-12-24
期刊：
JOURNAL OF MEDICINAL CHEMISTRY
影响因子：
7.3
作者：
Scott, Kevin A.;Qureshi, M. Haziq;Njardarson, Jon T.
通讯作者：
Njardarson, Jon T.

Phenols in Pharmaceuticals: Analysis of a Recurring Motif

DOI：
10.1021/acs.jmedchem.2c00223
发表时间：
2022-05-26
期刊：
JOURNAL OF MEDICINAL CHEMISTRY
影响因子：
7.3
作者：
Scott, Kevin A.;Cox, Philip B.;Njardarson, Jon T.
通讯作者：
Njardarson, Jon T.

Strategic Vinyl Sulfone Nucleophile β-Substitution Significantly Impacts Selectivity in Vinylogous Darzens and Aza-Darzens Reactions

DOI：
10.1021/acs.orglett.0c02448
发表时间：
2020-09-04
期刊：
ORGANIC LETTERS
影响因子：
5.2
作者：
Delost, Michael D.;Njardarson, Jon T.
通讯作者：
Njardarson, Jon T.

Dramatic Effect of γ-Heteroatom Dienolate Substituents on Counterion Assisted Asymmetric Anionic Amino-Cope Reaction Cascades

DOI：
10.1021/jacs.1c00745
发表时间：
2021-04-12
期刊：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
影响因子：
15
作者：
Das, Pradipta;Delost, Michael D.;Njardarson, Jon T.
通讯作者：
Njardarson, Jon T.

Oxidative Route to Indoles via Intramolecular Amino-Hydroxylation of o -Allenyl Anilines

通过邻联烯基苯胺的分子内氨基羟基化氧化为吲哚的路线

DOI：
10.1021/acs.joc.1c01379
发表时间：
2021
期刊：
The Journal of Organic Chemistry
影响因子：
0
作者：
Lauta, Nicholas R.;Williams, Ryan E.;Smith, David T.;Kumirov, Vlad K.;Njardarson, Jon T.
通讯作者：
Njardarson, Jon T.