Synthesis of dehydroperloline and of lactam antagonists of gamma - aminobutyric acid ( GABA )

by Duong Thach

Institution: University of Adelaide
Year: 1976
Keywords: dehydroperloline, aminobutyric acid antagonists, aminobutyric acid, chemical inhibitors
Record ID: 1032819
Full text PDF: http://hdl.handle.net/2440/37771


Part I of this thesis describes the synthesis of dehydro - perloline ( 3 ), a non basic material obtained from the degradation of the alkaloid perloline ( 1 ), the major alkaloid of New Zealand rye grass. Since a crucial reaction in this sequence involved a Schmidt reaction of fluorenols 4 or 5, some of the mechanistic aspects of this reaction have been investigated. Part II describes the synthesis of caprolactam derivatives 7 with the aim at finding new antagonists or analogues of the CNS inhibitory transmitter, gamma - aminobutyric acid ( GABA ). In Chapter 1, the synthesis of N - alkyl and N - arylcaprolac - tams is described. In Chapter 2, the synthesis, by several methods, of simple 3 - alkylcaprolactams is investigated. Chapter 3 describes synthetic methods for the preparation of 4 - substituted caprolactams. Chapter 4 presents the preparation of 5 - alkyl and 7 - alkyl - caprolactams by the Schmidt reaction on 4 - alkyl and 2 - alkylcyclo - hexanones. Chapter 5 describes some investigations of possible syntheses of 6 - alkylcaprolactams. Chapter 6 contains the results of testing of some lactams and thiolactams as well as their structure - activity relationships.