NOVEL RING-ENLARGEMENT CHAIN-EXTENSION REACTION

新型扩环扩链反应

• 批准号: 3297054
• 负责人: PAUL DOWD
• 金额: $ 9.08万
• 依托单位: UNIVERSITY OF PITTSBURGH AT PITTSBURGH
• 依托单位国家: 美国
• 财政年份: 1988
• 资助国家: 美国
• 起止时间: 1988-04-01 至 1993-03-31
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/3297054
• 关键词: aminoacid; benzazepines; chemical chain length; chemical reaction; cyclic compound; drug design /synthesis /production; heterocyclic compounds

A novel ring expansion and chain extension reaction has been discovered. The new reaction is completely regiospecific, takes place in excellent yield and appears to be capable of very broad application and extension, particularly in the area of medium- sized rings. Accordingly, it is proposed to extend the method to include heterocyclic compounds with emphasis on the pharmacologically useful benzazepines and dibenzazepines. Application to the synthesis of optically active beta-amino acids will be explored. Vinylogous ring expansion and inter- and intramolecular olefin trapping experiments will be carried out. The latter can yield new, efficient annulation methods. In addition to developing the one-carbon ring expansion, preliminary experimental findings have given positive results for three- and four-carbon ring expansions which open many new opportunities. These coupled with multiple ring expansion of keto diesters and diketo tetraesters provide a wealth of opportunity for elaboration of single and fused medium ring systems. The mechanistic premises underlying the reaction will also be examined.

报道了一种新的扩环扩链反应， 发现了 新的反应是完全区域特异性的， 在良好的产量和地方似乎能够非常广泛 应用和推广，特别是在中等教育领域， 大小戒指 因此，建议将该方法扩展到 包括杂环化合物， 有用的苯并氮杂卓和二苯并氮杂卓。 光学活性β-氨基酸的合成 将被探索。 乙烯基开环膨胀和间-和 将进行分子内烯烃捕获实验。 后者可以产生新的、有效的成环方法。 在 除了开发单碳环膨胀，初步 实验结果对三个和 四碳环的扩张带来了许多新的机会。 这些与酮基二酯的多环膨胀结合， 二酮基四酯提供了大量的机会， 单环和稠环系统。 机械论 反应的基本前提也将被研究。