SYNTHESIS AND REACTIONS OF SOME NEW 3-AMINO-2-SUBSTITUTED THIENOQUINOLINES

Article abstract of DOI:10.1135/cccc19922359

Reaction of 3-cyano-quinolin-2(1H)-thione (II) with ω-bromoacetophenones gave 3-amino-2-aroyl-thieno<2,3-b>quinolines (IVa - IVd).Whereas, interaction of II with chloroacetanilides yielded the corresponding thioethers Va - Vc which cyclized into 3-amino-2-arylcarbamoylthiene<2,3-b>quinolines (VIa - VIc) on treatment with ethoxide.Compounds VIa - VIc were reacted with nitrous acid, triethyl orthoformate and carbon disulfide to afford the fused polycyclic compounds VIIa - VIIc, VIIIa - VIIIc, and IXa - IXc, respectively.Also, treatment of IXa - IXc with ethyl iodide gave 3-ethylthio derivatives Xa- Xc.Moreover, refluxing of VIa - VIc with acetic anhydride resulted in the formation of oxazinone XI which recyclized into pyrimidinones XIIIa - XIIIc upon reaction with aromatic amines.