Experimental and Computational Study on the Debenzylation of (2,4-dimethoxybenzyl)-protected 1,3-diazaoxindoles

Authors

  • Eszter Kókai
    Affiliation

    Department of Materials Technology, GAMF Faculty of Engineering and Computer Science, John von Neumann University, Kecskemét, Hungary; Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Budapest, Hungary; Directorate of Drug Substance Development, Egis Pharmaceuticals Plc., Budapest, Hungary

  • Benjámin Kováts
    Affiliation

    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Budapest, Hungary

  • Balázs Komjáti
    Affiliation

    Servier Research Institute of Medicinal Chemistry, Budapest, Hungary

  • Balázs Volk
    Affiliation

    Directorate of Drug Substance Development, Egis Pharmaceuticals Plc., Budapest, Hungary

  • József Nagy
    Affiliation

    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Budapest, Hungary

https://doi.org/10.3311/PPch.11306

Abstract

The introduction and removal of the 2,4-dimethoxybenzyl (DMB) moiety was studied in order to use it as a protecting group in the synthesis of diverse drug candidates containing the 1,3-diazaoxindole scaffold. The debenzylation of C(5)-unsubstituted and C(5)-isopropylidene-substituted 1,3-diazaoxindoles was investigated under various conditions. The DMB group could only be removed from the latter derivative using triflic acid. This observation can most likely be explained with electronic effects. In order to get a deeper insight into the reaction mechanism, quantum chemical calculations have been performed.

Keywords:

1, 3-diazaoxindole, dimethoxybenzyl group, debenzylation, DFT, reaction mechanism

Published Online

2017-11-23

How to Cite

Kókai, E., Kováts, B., Komjáti, B., Volk, B., Nagy, J. “Experimental and Computational Study on the Debenzylation of (2,4-dimethoxybenzyl)-protected 1,3-diazaoxindoles”, Periodica Polytechnica Chemical Engineering, 61(4), pp. 264–269, 2017. https://doi.org/10.3311/PPch.11306

Issue

Vol. 61 No. 4 (2017)

Section

Articles