Development of Novel Stereocontrolled Synthetic Methods Using Hydroxy- and Amino-azoalkenes

美国国家科学基金会化学部化学合成项目通过该奖项支持休斯顿大学Don Coltart教授的研究，以开发构建含氮和含氧杂环的新方法。杂环是在许多化合物中发现的环状或环状分子结构，例如药物。在现有药物中发现的绝大多数含氮和含氧杂环具有扁平或圆盘状结构。从这些相对简单的扁平杂环转向具有更大三维度的杂环可能有利于改善旨在开发新药的努力。为了解决这个问题，Coltart研究小组正在开发各种合成工具和策略，以使这种三维含氮和含氧的杂环能够有效而简单地制造出来。这个项目的教育方面是针对研究生和本科生在动手实验室研究方面的培训。Coltart教授还提高了早期理科本科学生对化学科学非传统职业道路的认识。Coltart教授和他的学生开发了利用3-氨基-1-偶氮丙烯和3-羟基-1-偶氮丙烯（分别为AAPs和HAPs）合成饱和和部分饱和（SPS） N-和o-杂环的新方法。这些化合物可用于合成具有重要生物学意义的天然产物、药物和其他化合物。创建研究小组证实aap,也许不久展览3-dipolar反应,可以加上合作伙伴提供SPS N -和O-heterocycles偶极子,分别。许多偶极子可以与aap和HAPs结合，并以立体控制的方式用于生成各种杂环化合物，包括γ -内酯、γ -内酰胺、四氢呋喃和吡咯烷。这项工作的更广泛的影响包括招收来自代表性不足的群体的学生进入化学科学，以及一个外展计划，向本科理科学生介绍化学教育可以为他们提供的非常广泛的非传统职业机会。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。

With this Award, the Chemical Synthesis Program of the NSF Division of Chemistry is supporting the research of Professor Don Coltart of the University of Houston to develop novel ways of constructing nitrogen- and oxygen-containing heterocycles. Heterocycles are cyclic or ring-shaped molecular structures found in many compounds, such as pharmaceutical drugs. The vast majority of nitrogen and oxygen-containing heterocycles that are found in existing pharmaceuticals have a flat or disk-like structure. Moving away from these relatively simple flat heterocycles to ones that have greater three dimensionality may be beneficial in improving efforts aimed at developing new medicines. As a means of addressing this, the Coltart research group is developing a variety of synthetic tools and strategies to enable such three-dimensional nitrogen- and oxygen-containing heterocycles to be made effectively and simply. The educational aspects of this project are directed at the training of both graduate and undergraduate students in hands-on laboratory research. Professor Coltart also increases the awareness of early career undergraduate science students with regard to nontraditional career pathways in the chemical sciences. Professor Coltart and his students develop novel approaches to the synthesis of saturated and partially saturated (SPS) N- and O-heterocycles using 3-amino-1-azopropenes and 3-hydroxy-1-azopropenes (AAPs and HAPs, respectively). These are compounds can be applied to the synthesis of biologically important natural products, drugs, and other compounds. The Coltart research group established that AAPs and HAPs exhibit 1,3-dipolar reactivity and can be coupled with partner dipoles to provide SPS N- and O-heterocycles, respectively. Numerous partner dipoles are available to engage AAPs and HAPs and are being used to generate a wide range of such heterocyclic compounds in a stereocontrolled way, including gamma-lactones, gamma-lactams, tetrahydrofurans, and pyrrolidines. Broader impacts of this work include the recruitment of students from under-represented groups to the chemical sciences, as well as an outreach program to educate undergraduate science students about the very broad range of nontraditional career opportunities available to them with a chemistry education.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.