Synthesis of Some New N-[1-(Benzocoumarin-3`- yl)Ethylidene]Hydrazonothiazolidine, Thiazole and 1, 3, 4-Thidiazole Derivatives
نویسندگان
چکیده
Condensation of 3-acetylbenzo[5,6]coumarin (1) with hydrazine-carbodithioate esters and/or thiocarbohydrazide gave the corresponding N-[1-(benzocoumarin-3`-yl)ethylidene]hydrazonecarbodithioate (2a,b) and 1,5-bis[1-(benzocoumarin3`-yl)ethylidene]thiocarbohydrazide (3) respectively. Treatment of 2a with ethanolic ammonia solution and/or amines gave the corresponding thiosemicarbazone derivatives (4a-f). The reactions of 4a-f with ethyl bromoacetate/AcONa and ω-bromo derivatives were investigated, where thiazolidinones 5, 6 and thiazoles (9a,b) were obtained. Moreover, hydrazonecarbodithioate (2) underwent heterocycliczation upon treatment with hydrazonoyl halides (10) with Et3N to give the corresponding 2,3-dihydro-1,3,4-thiadiazoles (11a-d) via 1,3-dipolar cycloaddition and/or nuclophilic substiution. The structures of the new derivatives were elucidated by elemental analysis, IR, PMR and mass spectra.
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