Treatment of 1-[6-hydroxy-4-methoxybenzofuran-5-yl]ethanone (1) with cinnamaldehyde gave 1-[6-hydroxy-4-methoxybenzofuran-5-yl]-5-phenylpenta-2,4-diene-1-one (2) which reacted with formaline and 4-chloroniline to give benzofuran derivative (3) according to Mannich reaction. Interaction of 2 with 20% of sulphuric acid, malononitrile, ethylcyano acetate, phenyl hydrazine and guanidine hydrochloride afforded the corresponding furo[3,2-g]chromon-5-one (4), pyridine, pyrazole and pyrimidine derivatives  (5-8).  Also,  compound 8 reacted with phosphorus-oxychloride in dimethyl formamide and p-flurobenzylidenemalononitrile to give formyl and pyrimidopyrimidene derivatives (10, 12).