Kohn, Harold2022-06-222022-06-22197619763011600https://hdl.handle.net/10657/9833Selectedly substituted imidazolidinethiones and thioimidazolines were synthesized because of their close structural relationship to biotin and known CNS depressant agents. N-carbomethoxy-2-allylthioimidazoline and N-carbomethoxy-2-p-fluorobenzylthioimidazoline are both active methylene compounds. Treatment of these substrates with potassium tert.-butoxide did not lead to an intramolecular transfer of the carbomethoxy group. In each case, only the corresponding S-substituted thioimidazoline was isolated. An examination of the thermal reactivity of N-acetyl-2-allylthioimidazoline and N-carbomethoxy-2-allylthioimidazoline was undertaken. Thermolysis of N-acetyl-2-allylthioimidazoline (145[degrees]C, 72 hr) gave the N,N'-disubstituted isomer, while N-carbomethoxy-2-allylthioimidazoline (170[degrees]C, 72 hr) gave N-methyl-N'-allylimidazolidinethione and N-allylimidazolidinethione. Evidence for a [3,3]sigmatropic rearrangement in these reactions was gleaned from thermolysis of N-acetyl-2-crotylthioimidazoline (145[degrees]C, 17 hr). The only product isolated in this reaction was N-acetyl-N'-(3'-butenyl)-imidazolidinethione. The imidazolidinethiones and thioimidazolines synthesized were evaluated for their CNS depressant and anticonvulsant properties in mice. N-carbomethoxy-2-p-fluorobenzylthioimidazoline and N-acetyl-2-p-fluorobenzylthioimidazoline were the most active compounds, exhibiting strong anticonvulsant and CNS depressant effects.application/pdfenThis item is protected by copyright but is made available here under a claim of fair use (17 U.S.C. Section 107) for non-profit research and educational purposes. Users of this work assume the responsibility for determining copyright status prior to reusing, publishing, or reproducing this item for purposes other than what is allowed by fair use or other copyright exemptions. Any reuse of this item in excess of fair use or other copyright exemptions requires express permission of the copyright holder.Thesisreformatted digital