A prototype solid phase synthesis of pteridines and related heterocyclic compounds

C.L. Gibson, S. La Rosa, C.J. Suckling

Research output: Contribution to journalArticle

28 Citations (Scopus)

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.
LanguageEnglish
Pages1909-1918
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume1
Issue number11
DOIs
Publication statusPublished - 30 Apr 2003

Fingerprint

Pteridines
Heterocyclic Compounds
heterocyclic compounds
Solid-Phase Synthesis Techniques
Sulfides
resins
solid phases
cleavage
alkylates
Resins
prototypes
nitration
Nitration
Purines
purines
rings
Cyclization
Polystyrenes
pyrimidines
synthesis

Keywords

  • solid phase synthesis
  • pteridines
  • heterocyclic compounds
  • bicyclic polyaza heterocycles
  • purines
  • deazapurines
  • thioether
  • polystyrene resin
  • nucleophilic substitution
  • intrinsic reactivity

Cite this

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title = "A prototype solid phase synthesis of pteridines and related heterocyclic compounds",
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.",
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A prototype solid phase synthesis of pteridines and related heterocyclic compounds. / Gibson, C.L.; La Rosa, S.; Suckling, C.J.

In: Organic and Biomolecular Chemistry, Vol. 1, No. 11, 30.04.2003, p. 1909-1918.

Research output: Contribution to journalArticle

TY - JOUR

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AU - La Rosa, S.

AU - Suckling, C.J.

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KW - solid phase synthesis

KW - pteridines

KW - heterocyclic compounds

KW - bicyclic polyaza heterocycles

KW - purines

KW - deazapurines

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KW - polystyrene resin

KW - nucleophilic substitution

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