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.

ORCID iDs

Guiney, D., Gibson, C.L. ORCID logoORCID: https://orcid.org/0000-0003-4948-1266 and Suckling, C.J.;
  • Item type:Article
    ID code:887
    Dates:
    Date
    Event
    3 January 2003
    Published
    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
    Depositing user: Allison Crawford
    Date deposited:26 Apr 2006
    Last modified:19 Mar 2021 04:41
    URI:https://strathprints.strath.ac.uk/id/eprint/887
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