Abstract
Two- and three-component condensations of paraformaldehyde with trifluoromethanesulfonamide, acetamide, trifluoroacetamide, 1H-benzotriazole, methanesulfonamide, and malonamide were studied. N-Hydroxymethyl derivatives of trifluoroacetamide and 1H-benzotriazole reacted with trifluoromethanesulfonamide to give N-(trifluoroacetylaminomethyl)- and N-(1H-benzotriazol-1-ylmethyl)-substituted derivatives of tri-fluoromethanesulfonamide, as well as N,N′-methylenebis(trifluoromethylsulfonamide) and N-(trifluoromethyl-sulfonylaminomethyl)trifluoroacetamide as transamination products. Three-component condensation of trifluoromethanesulfonamide with paraformaldehyde and methanesulfonamide led to the formation of 1-methylsulfonyl-3,5-bis(trifluoromethylsulfonyl)hexahydro-1,3,5-triazine, and the reaction of trifluoromethanesulfonamide with paraformaldehyde and malonamide gave 4,10-bis(trifluoromethylsulfonyl)-2,4,8,10-tetraazaspiro-[5.5]undecane-1,7-dione whose structure was proved by X-ray analysis.
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Original Russian Text © V.I. Meshcheryakov, Yu.S. Danilevich, M.Yu. Moskalik, N.Yu. Stetsyura, V.E. Zavodnik, V.K. Bel’skii, B.A. Shainyan, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 6, pp. 799–805.
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Meshcheryakov, V.I., Danilevich, Y.S., Moskalik, M.Y. et al. Reactions of trifluoromethanesulfonamide with amides and paraformaldehyde. Russ J Org Chem 43, 793–800 (2007). https://doi.org/10.1134/S1070428007060012
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DOI: https://doi.org/10.1134/S1070428007060012