The alkylation of 5,5-disubstituted N-[4-methyl-3-phenylfuran-2(5 H)-ylidene]-N′-phenylthioureas with ethyl chloroacetate in the presence of potassium carbonate at a ratio of 1:1:0.6 led to the...

The reaction of 5,5-disubstituted 4-methyl-3-phenyl-2,5-dihydrofuran-2-imines with phenyl isothiocyanate afforded N-[5,5-disubstituted-4-methyl-3-phenylfuran-2(5 H)-ylidene]- N′-phenylthioureas.

As examples of “Click Chemistry”, the reaction of 1-(oxiran-2-ylmethyl)piperidine with several 1,2,4-triazoles derivatives was studied. As a result, the reaction shows that the oxirane ring opens regiospecifically, according to Krasusky’s rule, without using a catalyst. The basic nitrogen present in 1-(oxiran-2-ylmethyl)piperidine has a catalytic (anchimer) effect.

The corresponding N-alkyl derivatives were synthesized by alkylation of 5,5-disubstituted N-[4-methyl-3-phenylfuran-2(5H)-ylidene]-N′-phenylthiocarbami­des with methacrylate and acrylo­nitrile using a catalytic amount of sodium methylate.

The reaction of 2-[1-(4-methyl-5,5-R¹,R²-2-oxo-2,5-dihydrofuran-3-yl)ethylidene]­hydrazine-1-carbothioamides with allyl and propargyl bromides in the presence of a catalytic amount of sodium methylate afforded the corresponding S-derivatives. The reaction with 2-bromoacetophenone under similar conditions afforded the corresponding dihydrothiazoles, 5,5-disubstituted 4-methyl-3-(1-{[4-phenylthiazol-2(3H)-ylidene]hydrazono}ethyl)furan-2(5H)-ones. The antiradical and anticholinesterase properties of the synthesized compounds were studied. It was found that they possess moderate antiradical and high antibutyrylcholinesterase activities.