Treatment of o-chlorophenyl beta-ketoenolates 1 with carbon disulfide in the presence of sodium hydride and subsequent alkylation with CH-acidic halocompounds affords the thieno[2,3-b]-4H-[1]benzothiin-4-ones 3. Reaction of 1 with phenyl isothiocyanate leads to thiophenes 6 which undergo intramolecular cyclization yielding thieno[2,3-b]quinolin-4-ones 7.