Abstract Ringcontraction of 2,4,6-triarylpyrylium perchlorates by use of sodium nitrite mediated by ionic liquid has been used as a new, direct, and environmentally benign method for synthesis of bioactive 2-aroylfuran and novel 3,5-diaroyl-4-arylisoxazole derivatives in excellent yields. The versatility of the approach enables rapid and simple access to these pharmaceutically important compounds