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Condensation‐ring Expansion Reaction of Formyl[2.2.1]bicyclic Carbinols with Para ‐substituted Phenyl Amines: Application to the Preparation of [3.2.1]bicyclic N ‐aryl‐1,2,3‐oxathiazolidine‐2‐oxide Agents
Author(s) -
Yang TeFang,
Chen LiHsun,
Kao LiTa,
Chuang ChihHsiang,
Chen YongYen
Publication year - 2012
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201100517
Subject(s) - bicyclic molecule , chemistry , aryl , medicinal chemistry , camphor , stereospecificity , stereochemistry , organic chemistry , catalysis , alkyl
Individual reaction of camphene‐derived endo ‐formyl[2.2.1]bicyclic carbinol and that of camphor‐derived exo ‐formyl[2.2.1]bicyclic carbinol with parent and para ‐substituted phenyl amines gave regio‐ and stereospecific corresponding [3.2.1]bicyclic ( para ‐substituted) phenyl amino ketones. Mechanism of each reaction was discussed. Some camphor‐derived [3.2.1]bicyclic amino ketones were reduced to [3.2.1]bicyclic ( para ‐substituted) phenyl amino alcohols, which were then treated with mesyl chloride to provide [3.2.1]bicyclic N ‐phenyl/aryl‐1,2,3‐oxathiazolidine‐2‐oxide agents. The mechanism of this final reaction was discussed as well.