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Treatment of 2‐bromoacetylbenzofuran (2) with pyridine afforded its corresponding pyridinium bromide 3. The latter salt reacted with some activated alkenes and acetylenes to give the corresponding indolizine derivatives. Treatment of the salt 3 with benzylidenemalononitriles 9 afforded polysubstituted aniline derivatives, however with arylidenecyanothioacetamides 15 it gave the corresponding 4,5‐dihydrothiophenes. Bromide 3 also coupled with p‐chlorobenzenediazonium salt followed by ammonium acetate to give the corresponding 1,2,4,5‐tetrazine derivative. The biological activity of the newly synthesized compounds was examined and some of them were found to possess anticonvulsant and anti‐inflammatory activities.