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Reaction of 4-bromomethyl coumarins with schiff’s bases derived from salal and heterocyclic amines resulted in a tandem sequence leading to the formation of 3-heteroarylamino 2-4'coumarinyl 2,3-dihydrobenzofurans. The cis /trans diastereomeric ratio was estimated by 1 HNMR. Quantum chemical modeling studies provided a proof for very low energy difference between them and accounted for the inseparable mixture of the diasteromers. The synthesized compounds have been subjected to DNA cleavage studies.

Synthesis, modeling and biological studies on 4-2'(2, 3- dihydrobenzofuranyl) coumarins