New Strategies and Methods for Synthesis of Indoles and Carbazoles

通过这个奖项，化学合成项目支持纽约城市大学亨特学院郑胜平教授的基础研究。郑教授将开发新的方法来合成吲哚和咔唑，从商业上可获得的基石开始，如酚类和苯胺类，在一到三个步骤中。拟议的研究预计将对化学和制药行业产生影响，如合成具有生物活性和药用前景的天然产物，如lycoranine A和B， carbazomycin B和G.郑教授将利用有机合成的研究和教学作为发展科学技能的框架，并促进保留和招募在科学领域代表性不足的本科生群体。亨特学院拥有多元化的学生群体，并与当地高中建立了合作关系，这将为郑教授指导女性和其他代表性不足的群体的教育倡议提供一个绝佳的机会。本研究将以廉价的苯胺类/酚类为原料，探索吲哚类/氧吲哚类和氢咔唑类/咔唑类化合物的合成新策略和新方法。研究了以醌亚胺酮为原料合成吲哚/氧吲哚的方法。通过光重排，研究了由双环恶唑烷酮高效合成氢咔唑的方法。探讨了该方法在苯<s:1>烯酮合成中的应用。此外，还研究了以醌单酮和醌醇为原料合成咔唑的两种方法。一种是通过苯胺双离子加成到醌单酮，另一种是通过恶唑烷酮中间体通过钯催化的烯醇化芳基偶联。本研究开发的方法将对杂环合成做出重要贡献。

With this award, the Chemical Synthesis program is supporting fundamental research of Professor Shengping Zheng at Hunter College of the City University of New York. Professor Zheng will develop new methodologies for the synthesis of indoles and carbazoles beginning with commercially available building blocks, such as phenols and anilides, in one to three steps. The proposed research is expected to impact the chemical and pharmaceutical industries, as demonstrated by the synthesis of biologically active and pharmaceutically promising natural products such as lycoranine A and B, carbazomycin B and G. Professor Zheng will use research and teaching in organic synthesis as a framework for developing scientific skills and promoting retention and recruitment of groups of undergraduate students who are underrepresented in science. The Hunter College setting, with its diverse student body and partnerships with local high schools, will provide an excellent opportunity for directing Professor Zheng's educational initiative towards women and other underrepresented groups.In this research, new strategies and methods for the synthesis of indoles/oxindoles and hydrocarbazoles/carbazoles will be developed using inexpensive anilides/phenols as starting materials. Specifically, the synthesis of indoles/oxindoles from quinone imine ketals will be developed. An efficient synthesis of hydrocarbazoles from bicyclic oxazolidinones via a photo-rearrangement will also be investigated. Application of this method in the Büchi ketone synthesis will be explored. Furthermore, two syntheses of carbazoles from quinone monoketal and quinols will be studied. One is through anilide dianion addition to quinone monoketals and the other is through a palladium catalyzed enolate aryl coupling via an oxazolidinone intermediate. Methods developed in this research will make an important contribution to heterocyclic synthesis.