NOVEL RING-ENLARGEMENT CHAIN-EXTENSION REACTION

新型扩环扩链反应

• 批准号: 3297055
• 负责人: PAUL DOWD
• 金额: $ 9.65万
• 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/3297055
• 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.

提出了一种新的扩环扩链反应