An efficient taurine-catalyzed green multicomponent approach has been described for the first time to synthesize densely substituted therapeutic core dihydropyrano­[2,3-c]­pyrazoles. Applications of the developed synthetic strategies and technologies revealed the synthesis of a series of newly designed 1,4-dihydropyrano­[2,3-c]­pyrazoles containing isonicotinamide, spirooxindole, and indole moieties. Detailed in silico analysis of the synthesized analogues revealed their potential to bind wild-type and antibiotic-resistant variants of dihydrofolate reductase, a principal drug target enzyme for emerging antibiotic-resistant pathogenic Staphylococcus aureus strains. Hence, the synthesized dihydropyrano­[2,3-c]­pyrazole derivatives presented herein hold immense promise to develop future antistaphylococcal therapeutic agents.

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