Synthesis and reactions of 8-allylchromone-3-carboxaldehyde

Abstract

8-Allylchromone derivatives 5-7, 10 and 11 were prepared starting from 8-allylchromone-3-carboxaldehyde 4. Basic rearrangement of oxime 8 and/or carbonitrile 9 gave 8-allyl-2-aminochromone-3-carboxaldehyde 12. Chromeno[2,3-b] pyridines 14-20 were prepared via the reaction of 12 with malononitrile, cyanoacetamide, ethyl cyanoacetate, phenylthioacetonitrile, ethyl acetoacetate, ethyl benzoylacetate and barbituric acid. Structures of the new products have been deduced from elemental analysis and spectral data (IR, 1H NMR and mass spectra). © ARKAT USA, Inc.