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Reactions of 4-chloro-3-formyl-coumarin with primary amines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of 4-chloro-3-formylcoumarin with primary amines in the presence of triethylamine was studied. The reaction with aliphatic and aromatic amines leads to N-substituted 4-amino-3-formylcoumarins, whereas hetarylamines react primarily with the formyl group to form a mixture of the Z-and E-isomers of N-substituted 3-aminomethylenechroman-2,4-diones. Replacement of the triethylamine by anhydrous sodium acetate in the reaction of chlorocoumarin with 2-aminopyridines leads to the formation of the condensed benzopyranopyridopyrimidine system as a result of nucleophilic attack of the amino group by the chlorine atom at position 4.

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Authors and Affiliations

  1. Riga Technical University, Riga, Latvia

    I. Strakova, M. Petrova & A. Strakovs

  2. Latvian Institute of Organic Synthesis, Riga, Latvia

    S. Belyakov

Authors
  1. I. Strakova
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  2. M. Petrova
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  3. S. Belyakov
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  4. A. Strakovs
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 660–668, May, 2006.

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Strakova, I., Petrova, M., Belyakov, S. et al. Reactions of 4-chloro-3-formyl-coumarin with primary amines. Chem Heterocycl Compd 42, 574–582 (2006). https://doi.org/10.1007/s10593-006-0129-8

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  • DOI: https://doi.org/10.1007/s10593-006-0129-8

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