A one pot three component, copper catalyzed azide‐alkyne cycloaddition reaction has been employed for the synthesis of bis‐coumarinyl triazoles (A–D) using 4‐chloro, 4‐bromomethyl, 3‐bromoacetyl and 4‐bromomethyl‐1‐aza‐coumarins (I–IV), sodium azide, and coumarin propargyl ethers (V–IX) in moderate yields.
Coumarins and 8-hydroxy quinoline have received considerable attention in view of their wide ranging biological activities. 1,2 Coumarins have been investigated for their solid state photochemical dimerisation, 3 self association 4 and other structural features which have come to light by the study of their crystalline state. 5 We have found that the 4-aryloxymethyl coumarins 6 exhibit head-tail packing and centrosymmetric nature whereas 4-arylamino methyl coumarins 7 display layer like structure stabilised by intermolecular N-H•O bonding. Chemicals of analytical reagent grade were used directly without further purification. The compound 6-methylbromomethyl coumarin was synthesized according to an already reported procedure involving Pechmann cyclization of p-cresol with 4-bromoethylacetoacetate. 8 A mixture of 2.53 g of 6-methyl-bromomethyl coumarin (0.01 M) and 1.38 g of anhydrous potassium carbonate (0.01 M) was stirred for 30 min in dry acetone (30 mL); to this, 1.45 g of 6-methyl-bromomethyl coumarin (0.01 M) was added, and stirring was continued for 24 h (reaction mixture monitored). After completion of the reaction, the resulting mixture was poured into crushed ice. The separated solid was filtered and washed with 1:1 HCl (30 mL) and with cold water, dried and crystallized from DMF.
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