Regioselective cyclocondensation reactions of 1,3-bis(silyl enol ethers) with different electrophiles provide a convenient approach for the synthesis of 5-chlorosalicylates, arylphosphonates, 5-cyanosalicylates, 5-arylthio- and 5-benzylthio-6-phenylsalicylates, benzo[c]chromen-6-ones and chromeno[3,4-b]pyrrol-4(3H)-ones.