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Interaction of 2‐(bromoacetyl)‐3H‐benzo[f]coumarin (1) with salicylaldehyde afforded 2‐(2‐oxo‐2‐(3H‐benzo[f]coumarin‐2‐yl)ethoxy)benzaldehyde (2) which underwent self‐condensation in refluxing dimethylformamide (DMF) to afford 2‐(2‐benzofuroyl)‐3H‐benzo[f]coumarin (3). Treatment of 1 with o‐aminothiophenol (4) gave 2‐(2‐((2‐aminophenyl)thio)acetyl)‐3H‐benzo[f]coumarin (5). Refluxing of 5 in DMF led to formation of 2‐(4H‐[1,4]‐benzothiazin‐3‐yl)‐3H‐benzo[f]coumarin (6). Treatment of 1 with aryl amines 7a–d in boiling DMF gave 1‐aryl‐3‐hydroxybenzo[5,6]chromeno[4,3‐b]pyrrol‐4(1H)‐one (10a–d). Condensation of 11 with o‐phenylenediamine gave 2‐(2‐methyl‐2,3‐dihydro‐1H‐benzimidazol‐2‐yl)‐3H‐benzo[f]coumarin (12). Interaction of 2‐acetyl‐3H‐benzo[f]coumarin (11) with arylidene malonononitrile gave 4‐hydroxy‐2‐(3H‐benzo[f]coumarin‐2‐yl)‐5H‐dibenzo[c,f]chromen‐5‐one (16). All reaction products were characterized by analytical and spectral data. Novel compounds bioactivity as antitumor were examined for in vitro cytotoxicity against HepG‐2 and MCF‐7.

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