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Selective spectrofluorometric sensing is introduced for the analysis of non-steroidal anti-androgens, darolutamide, and thalidomide in pharmaceutical preparations and biofluids. An organic fluorophore, 2,4,8,10-tetramethylpyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine 2 was synthesized in our laboratories by new simple methods to act as a fluorescent reagent for the analysis of the studied drugs. Elemental and spectral analyses were performed to approve the fluorophore structure. The fluorophore possesses a fluorescence at λem 422 nm when excited at 328 nm. The interaction between the studied drugs and the fluorophore was found to be quenching. The quenching mechanisms were studied and interpreted through the Stern–Volmer relationship. Moreover, the Stern–Volmer constants were calculated for the quenching interactions of both drugs. The introduced method was validated for the estimation of darolutamide and thalidomide in dosage forms, plasma, and urine, offering good percentage recoveries.

Reaction of 3‐cyano‐4,6‐dimethyl‐2‐pyridone with ethyl chloroacetate afforded ethyl 2‐([3‐cyano‐4,6‐dimethylpyridin‐2‐yl]oxy)acetate 2 and ethyl 2‐(3‐cyano‐4,6‐dimethyl‐2‐oxopyridin‐1[2H]‐yl)acetate 3, the reaction product yield depend on the reaction condition (potassium carbonate concentration and reaction time). These compounds used as precursors to synthesize pyridine derivatives 4, 6‐10, 15, 17‐20, furopyridines 5, 16, pyrazolopyridine 12, pyridopyrazolopyrimidines 14a,b. The structure of the newly synthesized compounds was confirmed by spectral data (IR, NMR, and mass spectra) and elemental analysis.

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