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

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

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-diazaoxindo...

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Veröffentlicht in:Periodica polytechnica. Chemical engineering. 2017-01, Vol.61 (4), p.264-269
Hauptverfasser: Kókai, Eszter, Kováts, Benjámin, Komjáti, Balázs, Volk, Balázs, Nagy, József
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Quantum chemistry
Reaction mechanisms
Triflic acid
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container_title Periodica polytechnica. Chemical engineering.
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creator Kókai, Eszter
Kováts, Benjámin
Komjáti, Balázs
Volk, Balázs
Nagy, József
description 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.
doi_str_mv 10.3311/PPch.11306
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subjects Quantum chemistry
Reaction mechanisms
Triflic acid
title Experimental and Computational Study on the Debenzylation of (2,4-dimethoxybenzyl)-protected 1,3-diazaoxindoles
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