Abstract 6-Fluoro-4-methylcinnoline (IX) has been synthesized in eight steps from 4- fluoroaniline. A series of styryl and pyridylethenyl cinnolines have been prepared from 6- fluoro-4-methylcinnoline (IX), 4-methylcinnoline and 4-methylcinnoline-2-oxide. Furthermore, a series of 4-substituted benzylthiocinnolines have been prepared.