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Contributions towards the partial synthesis of 11-aza-steroids

Posted on:1960-11-11Degree:M.ScType:Thesis
University:The University of Western Ontario (Canada)Candidate:Huculak, Walter WarrenFull Text:PDF
GTID:2471390017974351Subject:Organic Chemistry
Abstract/Summary:
An attempt has been made to find a substance which would be suitable for synthesizing 11-aza-steroids.;This thesis concerns primarily the preparation of a compound in which ring C has been cleaved and which could be used for introducing a nitrogen atom in position 11 an outlined above.;Firstly, an attempt was made to open ring C of a material possessing a ring A/B cis configuration. It seemed that this could be achieved if certain ester groups are present in positions 3 and 20; the ester groups in positions 3 and 20 protecting the active oxygen functions. After several experiments, a substance with acetyl groups in positions 3 and 20 gave, in very small yields, a compound in which the ring C had been cleft.;Due to the low yield of the desired material possessing a ring A/B cis configuration, an attempt was made to cleave ring C in the trans series. After experiments analogous to those performed in the ring A/B cis series a better yield of a compound possessing a cleaved ring C was obtained. It seemed therefore, that a synthesis of an 11-aza-steroid could be more readily accomplished in the ring A/B trans series.;The 11-aza-steroids are derived from natural steroids by substituting a nitrogen atom for the carbon atom in position 11. This could be achieved by opening ring C in positions 9 and 12 (for example, by ozonolysis of a 9,11-unsaturated 12-ketone), introducing the nitrogen atom (for instance, by the formation of a 9-oxime), and then closing the ring.
Keywords/Search Tags:Ring, Nitrogen atom, A/B cis
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