New Strategies and Methods for Synthesis of Indoles and Carbazoles

吲哚和咔唑合成新策略和新方法

• 批准号: 1464543
• 负责人: Shengping Zheng
• 金额: $ 39万
• 依托单位: CUNY Hunter College
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2015
• 资助国家: 美国
• 起止时间: 2015-07-01 至 2020-06-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1464543&HistoricalAwards=false
• 关键词: New; Strategies; Methods; Synthesis; Indoles

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.

有了这个奖项，化学合成计划正在支持纽约亨特学院郑升平教授的基础研究。郑教授将开发吲哚和咔唑合成的新方法，从商业上可获得的构建块开始，如苯酚和苯胺，在一到三个步骤中。该研究有望影响化学和制药行业，如生物活性和药学上有前途的天然产物如石蒜碱A和B，卡巴霉素B和G的合成所证明的那样。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，并促进在科学领域代表性不足的本科生群体的保留和招聘。亨特学院的环境，其多样化的学生群体和与当地高中的合作伙伴关系，将提供一个很好的机会，指导郑教授的教育倡议，对妇女和其他代表性不足的群体。在这项研究中，新的策略和方法，合成吲哚/oxindoles和氢化咔唑/咔唑将开发使用廉价的苯胺/酚为起始原料。具体而言，将开发从醌亚胺缩酮合成吲哚/羟吲哚。本论文还将研究由双环恶唑烷酮通过光重排反应有效合成氢化咔唑的方法。探索了该方法在Büchi酮合成中的应用。此外，还研究了由醌单缩酮和醌醇合成咔唑的两种方法。一种是通过苯胺二价阴离子加成到醌单缩酮上，另一种是通过钯催化的烯醇化物芳基偶联经由恶唑烷酮中间体。本研究发展的方法将对杂环化合物的合成做出重要贡献。