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A One-Pot Synthesis of Highly Functionalized Purines
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    A One-Pot Synthesis of Highly Functionalized Purines
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    Univ. Grenoble Alpes, CNRS, DPM, 38000 Grenoble, France
    Univ. Grenoble Alpes, CEA, CNRS, BIG-LCBM, 38000 Grenoble, France
    § IMPMC, Sorbonne Universités, UPMC Univ. Paris 06, UMR CNRS 7590, Muséum National d’Histoire Naturelle, IRD UMR 206, IUC, Case 115, 4 Place Jussieu, 75005 Paris Cedex 05, France
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    Organic Letters

    Cite this: Org. Lett. 2017, 19, 23, 6360–6363
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    https://doi.org/10.1021/acs.orglett.7b03209
    Published November 10, 2017
    Copyright © 2017 American Chemical Society

    Abstract

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    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.

    Copyright © 2017 American Chemical Society

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.7b03209.

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    11. Renaud Zelli, Waël Zeinyeh, Jean‐Luc Décout. 6‐Chloropurine Ribonucleosides from Chloropyrimidines: One‐Pot Synthesis. Current Protocols in Nucleic Acid Chemistry 2018, 74 (1) https://doi.org/10.1002/cpnc.57
    12. Pierre Audebert, Clémence Allain. Triazines, Tetrazines, and Fused Ring Polyaza Systems. 2018, 399-426. https://doi.org/10.1016/B978-0-08-102788-2.00014-3

    Organic Letters

    Cite this: Org. Lett. 2017, 19, 23, 6360–6363
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.7b03209
    Published November 10, 2017
    Copyright © 2017 American Chemical Society

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