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Two Methods for the Preparation of 3-Dialkylaminomethyl Derivatives (Mannich Bases) of 4-Aminocoumarin: A New Type of Intramolecular Hydride Transfer
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1995
Year
Medicinal ChemistryDerivative (Chemistry)EngineeringBiochemistryIntramolecular Hydride TransferNew TypeSecondary AminesNatural SciencesPrimary Amine 6Organic ChemistryStereoselective SynthesisMannich BasesPharmacologyChemical DerivativeSynthetic ChemistryBiomolecular Engineering
The transformation of 4-alkylaminocoumarin-3-carbaldehydes (1b-f) by treatment with secondary amines 2a-i into 3-dialkylaminomethyl-4-aminocoumarins 4a-i via intramolecular hydride transfer is reported. The structure of 4 was ascertained by independent Mannich reaction of 4-aminocoumarin (5) yielding the 3-dialkylaminomethyl derivatives 4a-e. By treatment of 1e with primary amine 6 only the usual Schiff base 7 was obtained.