Issue 11, 2003
From the journal:

Organic & Biomolecular Chemistry

A prototype solid phase synthesis of pteridines and related heterocyclic compounds

Colin L. Gibson,a   Salvatore La Rosaa  and  Colin J. Suckling*a  

* Corresponding authors

a Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland
E-mail: c.j.suckling@strath.ac.uk

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.

Graphical abstract: A prototype solid phase synthesis of pteridines and related heterocyclic compounds

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Article information

DOI
https://doi.org/10.1039/B300798G
Article type
Paper
Submitted
23 Jan 2003
Accepted
31 Mar 2003
First published
30 Apr 2003

Org. Biomol. Chem., 2003,1, 1909-1918

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A prototype solid phase synthesis of pteridines and related heterocyclic compounds

C. L. Gibson, S. La Rosa and C. J. Suckling, Org. Biomol. Chem., 2003, 1, 1909 DOI: 10.1039/B300798G

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