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N-hetaryl-2,2-dichloroacetamidines

Pavlo V. Zadorozhnii, Vadym V. Kiselev, Aleksandr V. Kharchenko

Abstract


New feasible routes for the preparation of the novel 1,3,4-oxadiazole and 1,3-benzoxazole derivatives are described. These heterocycles have been directly obtained in one-pot reaction by refluxing of equivalent amounts of amines or hydrazides, N‑(2,2,2-trichloro-1-isothiocyanatoethyl)carboxamides in acetonitrile, then adding dicyclohexylcarbodi-imide with the 25% exess of dicyclohexylcarbodiimide (DCC) as a cyclodesulfurizing agent. A detailed study of the interaction of previously obtained 1,3,4-oxadiazoles and 1,3-benzoxazoles with an excess of primary and secondary amines has shown that in all cases the conversion is accompanied by dehydrochlorination and substitution of the amide moiety to the aminogroup and with formation of the corresponding the N-hetaryl-2,2-dichloroacetamidines. The structures of the synthesized compounds have been fully characterized by IR, 1H NMR, mass spectrometric data, elemental analysis and X-ray crystallographic analysis.

Keywords


1,3,4-oxadiazole; 1,3-benzoxazole; hetarylamidines; dicyclohexylcarbodiimide

References


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DOI: http://dx.doi.org/10.15421/081412

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