REACTIONS OF 4-CHLORO-3-FORMYLCOUMARIN WITH PRIMARY AMINES

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.

How to Cite
Strakova, I.; Petrova, M.; Belyakov, S.; Strakovs, A. Chem. Heterocycl. Compd. 2006, 42, 574. [Khim. Geterotsikl. Soedin. 2006, 660.]

For this article in the English edition, see DOI 10.1007/s10593-006-0129-8