Syntheses of highly functionalised 6-substituted pteridines

D. Guiney, C.L. Gibson, C.J. Suckling

Research output: Contribution to journalArticle

30 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)664-675
Number of pages11
JournalOrganic and Biomolecular Chemistry
Volume1
Issue number4
DOIs
Publication statusPublished - 3 Jan 2003

Keywords

  • polyfunctional 6-substituted pteridines
  • 6-aldehydes
  • Alkene
  • ester
  • ketone
  • amide
  • cyano
  • oxime
  • bromo
  • methoxy
  • 2-thioalkyl-6-formylpteridines
  • osmium tetraoxide
  • dihydroneopterin aldolase

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