A new general synthetic method for the preparation of 6-thiopteridines has been developed. The method involves the addition of thiols to intermediate pyrimidine nitrones formed in situ by the reaction of 4-amino-5-nitrosopyrimidines with pyridinium-activated acetonitriles, acetates, acetophenones, and other methylketones. Ca. forty new pteridines were prepared by this method. The preparation of six new 6-pteridinyl ketones, two new 6- pteridinyl ketone thiosemicarbazones, and two new 6-sulfonylpteridines and their 4-acetamido derivatives is also reported. 4-Acetamido-2- amino-7-phenylpteridine 5-oxide was prepared by the reaction of 2- amino-4,6-diacetamido-5-nitrosopyrimidine with either phenylsulfonyl-acetophenone or phenacylpyridinium bromide. Evidence relating to the structure of the acylated 4-amino-5- nitrosopyrimidines used as intermediates in the aforementioned reactions is presented and discussed. Also included in the dissertation are detailed reviews of the following subjects: Pteridine antimalarials, 6-thiopteridines, 6- pteridinesulfonic acids, 6-pteridinesulfonamides, 6-pteridinyl ketones, and pteridine N-oxides.
College and Department
Chemistry and Biochemistry
BYU ScholarsArchive Citation
Parish, Walter Wesley, "The synthesis and properties of new potentially chemotheraputic [sic] pteridine derivatives" (1970). Theses and Dissertations. 8327.