UBC Theses and Dissertations
Synthesis of dispiro compounds and derivatives as potential medicinal agents Janis, Ronald Allen Joseph
The syntheses of 8-amino-16-azadispiro[188.8.131.52]heptadecan-16-one and its 8-chloroacetyl derivative are reported. The compounds were characterized by their infrared spectra and by elemental analysis of the latter compound. Data is presented for the attempted reaction of dimethylaminoacetic acid with 7-amino-14-azadispiro[184.108.40.206]pentadecan-15-one and 8-amino-16-azadispiro-[220.127.116.11]heptadecan-17-one using dicyclohexylcarbodiimide as the condensing reagent. The reduction of the product obtained from the latter reaction is described. The addition of the ß-dimethylaminoethyl group to the 8-amino dispiro compound named above, in the presence of sodamide was also tried. A ß-dimethylaminoethyl derivative of 7,14-diazadispiro[18.104.22.168]penta-decane was synthesized by the lithium aluminum hydride reduction of the pentadecan-15-one analog. A correct elemental analysis was obtained for the unsaturated compound but the reduced derivative was identified only by its infrared spectrum. It was not determined whether substitution had occurred at the secondary or the lactam nitrogen. The reaction of chloroacetyl chloride with 7,14-diazadispiro[22.214.171.124]pentadecan-15-one using a variety of reaction conditions is described. Data is also presented for the attempted purification of the product obtained from the latter reaction; both thin layer and column chromatography were employed. The condensation reaction of 1-amino-cycloheptanecarbonitrile in the presence of sodium ethoxide and a trace of moisture does not yield the expected 8,16-diazadispiro[126.96.36.199]heptadecan-17-one.
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