Open AccessExperimental and Computational Study on the Debenzylation of (2,4-dimethoxybenzyl)-protected 1,3-diazaoxindoles
Author(s) -
Eszter Kókai,
Benjámin Kováts,
Balázs Komjáti,
Balázs Volk,
József Nagy
Publication year - 2017
Publication title -
periodica polytechnica. chemical engineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.322
H-Index - 19
eISSN - 1587-3765
pISSN - 0324-5853
DOI - 10.3311/ppch.11306
Subject(s) - moiety , triflic acid , quantum chemical , chemistry , derivative (finance) , combinatorial chemistry , computational chemistry , order (exchange) , mechanism (biology) , stereochemistry , medicinal chemistry , organic chemistry , catalysis , molecule , physics , quantum mechanics , business , finance
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.