The easily obtainable title compounds ethyl 5‐ and 3‐triflyloxy‐1H‐pyrazole‐4‐carboxylates (2 and 5) have been used as precursors in Sonogashira‐type cross‐coupling reactions with various alkynes to obtain the corresponding 5‐ and 3‐alkynyl‐4‐(ethoxycarbonyl)pyrazoles 3 and 6. Cyclization of the latter ortho‐difunctional synthons afforded different condensed pyrazoles such as pyrano[4,3‐c]pyrazol‐4(1H)‐ones and ‐4(2H)‐ones 7 and 10 as well as 1,5‐dihydro‐ and 2,5‐dihydro‐4H‐pyrazolo[4,3‐c]pyridin‐4‐ones 9 and 12, respectively. Suzuki coupling of triflate 2 with phenylboronic acids gave the corresponding 5‐arylpyrazoles. Heating of 5‐(3‐chlorophenyl)‐1‐phenyl‐1H‐pyrazole‐4‐carboxylic acid (16) with trifluoromethanesulfonic acid led to the formation of the unexpected tetracyclic system 18. Detailed NMR spectroscopic investigations were undertaken on all obtained products.