Ensembles of rings with a coumarin unit. 1. Synthesis of 3-(2-R-thiazol-4-yl)- and 3-(4-R-triazol-2-yl)coumarins

Article abstract of DOI:10.1007/BF02290865

We have synthesized 3-(2-R-thiazol-4-yl)coumarins (R = H, CH₃, CH₂CN, Ar) by condensation of 3-(α-bromoacetyl)coumarins with thioamides. We obtained 3-(4-R-thiazol-2-yl)coumarins (R = H, Ar) by several methods. By reaction of 2-cyanomethyl-4-phenylthiazole with 2-hydroxybenzaldehydes, we synthesized 2-imino-3-(4-phenylthiazol-2-yl)coumarins, which were converted to the corresponding coumarins by acid hydrolysis. For 3-(2-R-thiazol-4-yl)coumarins (R = CH₂CN), we carried out reactions with aromatic aldehydes. We propose alternative methods for synthesis of 2-[2-aryl(hetaryl)-1-cyanoethenyl]-4-(coumarin-3-yl)thiazoles. 1998 Plenum Publishing Corporation.