A facile and highly efficient metal‐free approach has been unfolded for the synthesis of novel dihydrothiochromeno[4,3‐c]pyrazoles using elemental sulfur as a powerful sulfurating reagent. This method includes sp2 C−H functionalization followed by sp2 C−NO2 group displacement using elemental sulfur as an odourless sulfur source activated by DABCO in DMSO. Using the developed synthetic strategy, a library of 29 novel dihydrothiochromeno[4,3‐c]pyrazoles, incorporating two pharmacologically important scaffolds has been synthesized in 52–76% yield with a broad substrate scope. A sensible mechanistic proposal has been projected based on control experiments.
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