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-Halocarbonyl compounds, including such derivatives as -chloroacetic acid and 2-halo ketones or phenacyl bromides, are widely used in organic synthesis for the preparation of different heterocyclic compounds [1][2][3][4][5][6][7][8][9]. We have previously shown that reaction of arylhydrazonothioacetamides with -halo ketones gives 1,3-thiazoles or 4,5-dihydrothiophenes depending on the electronic effects and steric factors of the substituents on the nitrogen atom of the thioamide fragment and the nature of the substituent in the aromatic ring [6-9]. The aim of our work is to determine the area of applicability of this reaction in the synthesis of thiophenes and to study the chemical properties of the heterocyclic compounds obtained.The reaction of the arylhydrazonothioacetamides 1a-h (which contain a tert-cycloalkylamine substituent in the thioamide group) with the -halo ketones 2a,c, chloroacetonitrile 2b, and 4-nitrobenzyl bromide 2d was carried out by heating in the presence of strong bases.As a result we obtained the series of 3-amino-2-arylazothiophenes 4a-m, the mechanism of formation of which can be represented as a nucleophilic addition of the methylene group to the carbon atom of the cyano group in the initially formed intermediate 3. The 1 H NMR spectra of the aminothiophenes 4a-m show the presence of a signal for the NH 2 group as two broad, one-proton singlets or a two-proton singlet in the region 9.00-10.10 ppm together with signals for the proton-containing parts of the substituents R, R 1 , and tert-cyclo-_______________ Dedicated to Academician V. N. Charushin on his 60th birthday.

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The reactions of 2 arylhydrazono 2 carbamoylacetamidoximes with orthoesters afford either 3 arylhydrazono 1,2,4 oxadiazoles or 1,2,3 triazoles, depending on the reactant structure.