SYNTHESIS OF FUSED HETEROCYCLIC COMPOUNDS

稠合杂环化合物的合成

• 批准号: 6182237
• 负责人: Albert Padwa
• 金额: $ 19.29万
• 依托单位: EMORY UNIVERSITY
• 依托单位国家: 美国
• 财政年份: 1999
• 资助国家: 美国
• 起止时间: 1999-09-01 至 2003-08-31
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/6182237
• 关键词: Diels Alder reaction; alkaloids; chemical synthesis; cyclization; nitrogenous heterocyclic compound; sulfur compounds

DESCRIPTION: (Applicant's Abstract) The overall objective of our research program involves the development of general, broadly applicable methods that makes use of organosulfur compounds for the construction of novel nitrogen containing heterocycles. Emphasis will be placed on new domino cyclization/cycloaddition cascade reactions of organosulfur derivatives for the construction of a variety of biologically interesting molecules. Among the reactions to be studied are cycloaddition reactions of mesoionic thio-substituted betaines, Diels-Alder reactions of thio-substituted heteroaromatics and new applications of the Pummerer reaction for heterocyclic synthesis. The project will also focus on using a variety of novel thio reagents for intramolecular cyclization. A number of inter and intramolecular variations of the tandem sequence will be explored which will provide access to the structural frameworks contained within the Amaryllidaceae, Aspidosperma, Erythrina, Pyrrolizidine, Quinolizidine, Sceletium and Vinca alkaloids. These complex nitrogen containing substrates are of interest as synthetic targets due to the wide range of biological properties they exhibit. A variety of pharmacological effects, including sedative, hypotensive, neuromuscular blocking, CNS depressant and skin disorder properties are associated with these compounds. The various synthetic strategies outlined in the proposal will lead to the rapid assembly of the basic core skeleton of various alkaloids and will provide quantities of material for detailed biological assay. The generation of biologically active compounds by new synthetic methods remains an important part of both health related and chemical research.

描述：（申请人的摘要）我们研究的总体目标 该计划涉及开发通用的、广泛适用的方法， 利用有机硫化合物构建新型氮 含有杂环。重点将放在新的多米诺骨牌上 有机硫衍生物的环化/环加成级联反应 构建各种具有生物学意义的分子。其中 要研究的反应是介离子的环加成反应 硫代甜菜碱，硫代甜菜碱的狄尔斯-阿尔德反应 杂芳烃及杂环Pummerer反应的新应用 合成。该项目还将重点使用各种新型硫代化合物 分子内环化试剂。许多分子间和分子内 将探索串联序列的变化，这将提供访问 石蒜科、Aspidosperma 中包含的结构框架， 刺桐、吡咯里西啶、喹诺西啶、Sceletium 和长春花生物碱。这些 复杂的含氮底物作为合成目标受到关注，因为 它们表现出广泛的生物学特性。各种 药理作用，包括镇静、降血压、神经肌肉作用 阻断、中枢神经系统抑制剂和皮肤病特性与这些有关 化合物。提案中概述的各种合成策略将导致 快速组装各种生物碱的基本核心骨架并将 为详细的生物测定提供大量材料。的一代 通过新的合成方法获得生物活性化合物仍然是一个重要的领域 健康相关研究和化学研究的一部分。