Studies on Pteridines and Related Pyrazines

Dick, George P. G (1956) Studies on Pteridines and Related Pyrazines. PhD thesis, University of Glasgow.

Abstract

1. A new method is reported for the synthesis of 2-amino-4-hydroxypteridines, namely, the condensation of 2-chloro-3-methoxycarbonylpyrazinss with guanidine salts. This method will enable the 2-position in this important type of pteridino molecule to be labelled isotopically at the final stage in the synthesis. A route to 2-chloro-3-methoxycarbonylpyrazines starting from readily available aliphatic compounds has been developed. The use of the aldehyde-binding reagent, sodium hydrogen sulphite in the condensation of alpha:beta-dicarbonyl compounds with aminomalonamide has been shown to facilitate the reaction. Contrary to a previous report, the condensation of methyl glyoxal with aminomalonamide, with or without an aldehyde-binding reagent present, gave 2-hydroxy-6-methylpyrazino-3-carboxyamide. This result has since been supported by more recent publications by two independent research teams. 2. A method has been developed for the synthesis of 2:8-dihydro-4-hydroxy-2-imino-8-methylpteridines from pyrazine derivatives This preliminary investigation will probably provide a suitable synthetic route to pteridine Mg glycosides, which have been postulated to occur in nature. The methylation of 2-hydro-5:6-diphenyl-3-carboxylic acid and its methyl ester have been studied.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry
• Date of Award: 1956
• Depositing User: Enlighten Team
• Unique ID: glathesis:1956-79203
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 05 Mar 2020 11:28
• Last Modified: 05 Mar 2020 11:28
• URI: https://theses.gla.ac.uk/id/eprint/79203