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A prototype solid phase synthesis of pteridines and related heterocyclic compounds

Gibson, C.L. and La Rosa, S. and Suckling, C.J. (2003) A prototype solid phase synthesis of pteridines and related heterocyclic compounds. Organic and Biomolecular Chemistry, 1 (11). pp. 1909-1918. ISSN 1477-0520

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Abstract

The development of a versatile solid phase synthesis of bicyclic polyaza heterocycles including pteridines, purines, and deazapurines is described. The strategy comprises the linking of a pre-formed pyrimidine through a thioether at the 2 or 4 position to a polystyrene resin, the cyclisation of the second ring, and the direct or oxidative cleavage of the product from the resin by nucleophilic substitution. This provides not only for substituent variation in the second ring, but also for variation at the site of cleavage. Limitations in the scope of the methodology are set by the intrinsic reactivity of pyrimidinyl 2- or 4-thioethers which, whilst undergoing ready nitration at C5, are surprisingly difficult to alkylate and acylate.

Item type: Article
ID code: 888
Keywords: solid phase synthesis, pteridines, heterocyclic compounds, bicyclic polyaza heterocycles, purines, deazapurines, thioether, polystyrene resin, nucleophilic substitution, intrinsic reactivity, Chemistry
Subjects: Science > Chemistry
Department: Faculty of Science > Pure and Applied Chemistry
Unknown Department
Related URLs:
    Depositing user: Allison Crawford
    Date Deposited: 26 Apr 2006
    Last modified: 12 Mar 2012 10:36
    URI: http://strathprints.strath.ac.uk/id/eprint/888

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