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Syntheses of highly functionalised 6-substituted pteridines

Guiney, D. and Gibson, C.L. and Suckling, C.J. (2003) Syntheses of highly functionalised 6-substituted pteridines. Organic and Biomolecular Chemistry, 1 (4). pp. 664-675. ISSN 1477-0520

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Abstract

Methods for the synthesis of polyfunctional 6-substituted pteridines from the corresponding 6-aldehydes are described. Alkene, ester, ketone, amide, cyano, oxime, bromo, methoxy and dihydroxy functional groups have all been introduced principally through improved methodologies for Wittig reactions using 2-thioalkyl-6-formylpteridines as substrates. Further modification of the alkenes derived from the Wittig reactions was difficult but selective conversion to the vic-diol was possible using ligand assisted catalysis with osmium tetraoxide. These methods are a component of an extensive methodology for the preparation of compounds that might serve as modulators of tetrahydrobiopterin activity or as inhibitors of dihydroneopterin aldolase.

Item type: Article
ID code: 887
Keywords: polyfunctional 6-substituted pteridines, 6-aldehydes, Alkene, ester, ketone, amide, cyano, oxime, bromo, methoxy, 2-thioalkyl-6-formylpteridines, osmium tetraoxide, dihydroneopterin aldolase, Chemistry, Biochemistry, Organic Chemistry, Physical and Theoretical Chemistry
Subjects: Science > Chemistry
Department: Faculty of Science > Pure and Applied Chemistry
Related URLs:
    Depositing user: Allison Crawford
    Date Deposited: 26 Apr 2006
    Last modified: 04 Sep 2014 11:48
    URI: http://strathprints.strath.ac.uk/id/eprint/887

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