Abstract
Multicomponent heterocyclization of aliphatic amides with H2S and CH2O (1:3:2) in water-organic solvent mixture in the presence of BuONa led to the formation of 1,3,5-dithiazinane in high yield (30–95%) and with high selectivity (100%). Under these conditions benzamide gave 3,5-dibenzoyl-1,3,5-thiadiazinane in 74% yield, whereas due to ortho-effect the acetylsalicylamide with H2S and CH2O in a system BuOH-H2O without BuONa formed N-acetylsalicyloyl-1,3,5-dithiazinane (80%). Heterocyclization of α-aminosuccinic acid monoamide depending on the H2S and CH2O concentration occurred either at one or both NH2 yielding respectively mono-or bisdithiazinanes.
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Original Russian Text © V. R. Akhmetova, R.R. Khairullina, G.R. Nadyrgulova, R.V. Kunakova, U.M. Dzhemilev, 2008, published in Zhurnal Organicheskoi Khimii. 2008, Vol. 44, No. 2, pp. 200–206.
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Akhmetova, V.R., Khairullina, R.R., Nadyrgulova, G.R. et al. Multicomponent heterocyclization of carboxamides with H2S and CH2O. Russ J Org Chem 44, 190–196 (2008). https://doi.org/10.1134/S1070428008020036
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DOI: https://doi.org/10.1134/S1070428008020036