Abstract
Photo-oxygenation reaction was performed on eugenol (1) (2methoxy-4-(2'-propenyl) phenol) in chloroform as a solvent and tetraphenyl porphrine (TPP) as singlet oxygen sensitizer. Irradiation of the reaction mixture was carried out by sodium lamp at -20 °C for six hrs., during which dry oxygen was allowed to pass through the reaction mixture. Two hydroperoxides (3) and (4) were formed. Eugenol methyl ether (2) was also photo-oxygenated under the same conditions of eugenol, where only the side chain was photo-oxygenated at position C-1' to give product (5). In addition to the epoxide derivative of eugenol methyl ester (8) was prepared and its reaction with aminoantipyrine was carried out to give product (9). Product (8) could be considered as a DNAalkylating agent.
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