Self-condensation of 3-cyanothiochromone upon the action of benzyl- and phenethylamine

Article abstract of DOI:10.1007/s11172-010-0373-z

Reflux of 3-cyanothiochromone with benzylamine in toluene afforded 17-benzyl-6,7,14,15-tetrahydro-7,15-epiminobis(8H,16H-dithiochromeno)[2,3-b: 2′,3′-f][1,5]diazocine-6,14-dione, the self-condensation product of 2-amino-3-(benzyliminomethyl)thiochromone. Similar reaction with phenethylamine leads to 2-(thiochromon-3-yl)-5H-thiochromeno[2,3-d]-pyrimidin-5-one. Mechanism of formation of the dimeric products was considered.