5 years ago

A One-Pot Synthesis of Highly Functionalized Purines

A One-Pot Synthesis of Highly Functionalized Purines
Jean-Luc Décout, Benjamin Boucherle, Julien Alliot, Waël Zeinyeh, Romain Haudecoeur, Isabelle Callebaut, Renaud Zelli
Highly substituted purines were synthesized in good to high yields through a one-pot straightforward metal-free scalable method, using the Traube synthesis adapted to Vilsmeier-type reagents. From 5-amino-4-chloropyrimidines, new 9-aryl-substituted chloropurines and intermediates for peptide nucleic acid synthesis were prepared. Variant procedures allowing a rapid synthesis of ribonucleosides and 7-benzylpurine from 5-amidino-6-aminopyrimidines are also reported to illustrate the high potential of this versatile toolbox. This route appears to be particularly interesting in the field of nucleic acids for a direct and rapid access to various new 8-alkylpurine nucleosides.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b03209

DOI: 10.1021/acs.orglett.7b03209

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