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a b s t r a c tA series of new and novel coumarin-6-sulfonamides with a free C4-azidomethyl group have been synthesized as antimicrobials in three steps starting from 7-methyl-4-bromomethylcoumarin 1. The reaction of 1 with chlorosulfonic acid was found to yield the corresponding 6-sulfonylchloride 2, which when treated with sodium azide led to intermediate 3. The title sulfonamides 5a-y were obtained from the reaction of 3 with various aromatic amines 4 in refluxing benzene. The chemical structures of the compounds were elucidated by IR, NMR and LC-MS spectral data. All the synthesized compounds have been screened for their in vitro anti-bacterial and anti-fungal activities. Some of the compounds have been found to be active against both bacterial species at a concentration of 1 mg/mL.

A number of new 4-aryloxymethylcoumarins 3 and 5 have been obtained from the reaction of various 4-bromomethylcoumarins with 2-nitro-p-cresol 2 and 2,6-dibromo-p-cresol 4. NOE studies have been carried out on two compounds to ascertain their spatial proximity. p-cresol ethers 7 have been subjected to bromination in chloroform and the position of bromine has been established by diffraction studies. Cleavage of the ether linkage has been observed during an attempted nitration of ethers 7. Antimicrobial activity of all the compounds against five bacterial and five fungal species have been reported.

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