A simple approach to multifunctionalized N1-alkylated 7-amino-6-azaoxindole derivatives using their in situ stabilized tautomer form

作者: Nikolay T. Tzvetkov , Beate Neumann , Hans-Georg Stammler , Liudmil Antonov

DOI: 10.1016/J.TET.2016.08.055

关键词: Computational chemistryAlkylationOrganic chemistryIntramolecular forceTautomerIn situReactivity (chemistry)Structural isomerPyrroleAtomChemistry

摘要: A simple approach for the synthesis of multifunctionalized N1-alkyl 7-amino-6-azaoxindole derivatives was developed and investigated. Formation 5-amino- 7-amino-6-aza-2-oxindoles 12a 13a, respectively, achieved using an intramolecular reductive cyclization as a key step. Subsequent alkylation pyrrole N1 atom in led to desired N1-alkylated compounds 22a–24 comprising different functionalities. Alkylation 5-amino-substituted regioisomer 13a under same conditions used did not resulted products. To find plausible explanation observed differences reactivity, we investigated possible tautomers distribution their neutral ionized forms gas phase. The relevant physicochemical properties 23 were determined.

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