Efficient synthesis of 1,3,7-substituted xanthines by a safety-catch protection strategy

Matthew Allwood, Boorna Cannan, Daan M. F. van Aalten, Ian M. Eggleston

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    15 Citations (Scopus)

    Abstract

    An efficient synthesis of selectively N-substituted xanthine derivatives is described. Cyclocondensation of a suitably protected ammoimidazole with methyl-2-phenylthioethyl carbamate, followed by oxidation of sulfur to the sulfone, provides access to an orthogonally 1,7-protected xanthine, which may then be regioselectively alkylated and deprotected under mild conditions. (c) 2007 Elsevier Ltd. All rights reserved.

    Original languageEnglish
    Pages (from-to)12294-12302
    Number of pages9
    JournalTetrahedron
    Volume63
    Issue number50
    DOIs
    Publication statusPublished - 10 Dec 2007

    Keywords

    • Solid phase synthesis
    • Receptor antagonists
    • 1,3-substituted xanthines
    • Theophylline
    • Derivatives
    • Inhibitors
    • Expression
    • Asthma
    • Potent

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