SYNTHESIS OF SOME NEW HETEROCYCLIC COMPOUNDS CONTAINING THIENO[2,3-b]QUINOLINE MOIETY

Abstract

2-Cyano-3-amino-4-aryl-5, 6, 7, 8-tetrahydro-thieno[2,3-b]quinoline (1) reacted with carbon disulfide to give compound 2. Alkylation of 2 with different reagents gave the corresponding thioethers 3–7. Diazotisation of 1 furnished chloro derivative 8 which reacted with thiourea to give mercaptotriazine 9. Methylation of 9 yielded 10. On treatment of 8 with hydrazone hydrate, the expected hydrazinocompound 11 was obtained. Reaction of 11 with aromatic aldehydes, acetylacetone, acetic acid, acetic anhydride, carbon disulfide and nitrous acid gave compounds 12–17, respectively. The structures of all synthesized compounds were confirmed by elemental and spectral analysis.

Key Words:

• Thienoquinolines
• pyrimidine-dithiones
• pyrimidine-dithioethers
• chlorotriazines
• mercaptotriazines
• hydrazinotriazines and pyrazolyltriazines.