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Synthesis 1995; 1995(6): 633-634
DOI: 10.1055/s-1995-3971
short paper
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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

Ivo C. Ivanov* , Stoyan K. Karagiosov
  • *Department of Organic Chemistry, Faculty of Pharmacy, Higher Medical School, Dunav 2, 1000 Sofia, Bulgaria, Fax +359(2)876265
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Publication Date:
31 December 2000 (online)

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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.

hydride transfer - Mannich bases - 4-aminocoumarins

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