Catalysis of Nucleophilic Aromatic Substitutions in the 2,6,8-trisubstituted Purines and Application in the Synthesis of Combinatorial Libraries

Overview

Journal Mol Divers

Date 2003 Aug 30

PMID 12945741

Citations 1

Authors

Claudia Riva-Toniolo

Sascha Muller

Josette Schaub

Wolfgang K D Brill

Affiliations

Soon will be listed here.

Abstract

The following paper summarizes our work on compound libraries of 2,6,8-trisubstituted purines. This synthesis route on a polystyrene support begins with 2,6-dichloro purine making extensive use of catalysis. During the synthesis the polymer bound purines were brominated selectively on C8. The substitution reaction of C6-Cl by amines was found to be acid catalyzed. The substitution of C2-Cl by amines and aryls, as well as the substitution of a C8-Br by aryls, alkenyl and alkynyl groups can be catalyzed by transition metals. Under some bromination conditions novel selective oxidative transformations of 2-amino groups in 2,6-diamino purines have been found.

Citing Articles

Synthesis and anticancer activity of multisubstituted purines and xanthines with one or two propynylthio and aminobutynylthio groups.

Kowalska A, Pluta K, Latocha M Med Chem Res. 2018; 27(5):1384-1395.

PMID: 29706750 PMC: 5904222. DOI: 10.1007/s00044-018-2155-3.

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