Reaction of N(5-R-furan-2-ylmethylidene)anilmes with difluorocarbene, generated in CF₂Br₂/Pb*/Bu₄NBr/ultrasound system proceeds via 1,5-electrocyclization of intermediate azomethine ylides to give 6,6-difluorocyclopropa[b]furo[2,3-c]pyrrol-4(5H)-one or/and 4,4,6,6-tetrafluorocyclopropa[b]furo[2,3-c]pyrrole derivatives. Thermolysis of these compounds under solvent-free conditions gives rise to 2,5-disubstituted 7-fluoro-4,5-dihydrofuro[3,2-c]pyridine-4(5H)-ones in high yields.