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α-Thioureidoalkylation of functionally substituted ureas: I. Tandem cyclization and esterification in reactions of N-(carboxyalkyl)ureas with 1,3-dialkyl-4,5-dihydroxy-4,5-diphenylimidazolidine-2-thiones in alcohols

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Abstract

Acid-catalyzed reactions of N-(carboxyalkyl)ureas with 1,3-dialkyl-4,5-dihydroxy-4,5-diphenylimidazolidine-2-thiones in methanol or propan-2-ol led to the formation of previously unknown ω-(4,6-dialkyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)alkanoic acids and their methyl and isopropyl esters. The structure of some esters was proved by X-ray analysis. Methyl (4,6-diethyl-2-oxo-3a,6adiphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)acetate showed anxiolytic effect.

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Correspondence to A. N. Kravchenko.

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Original Russian Text © V.V. Baranov, G.A. Gazieva, Yu.V. Nelyubina, A.N. Kravchenko, N.N. Makhova, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 10, pp. 1535–1542.

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Baranov, V.V., Gazieva, G.A., Nelyubina, Y.V. et al. α-Thioureidoalkylation of functionally substituted ureas: I. Tandem cyclization and esterification in reactions of N-(carboxyalkyl)ureas with 1,3-dialkyl-4,5-dihydroxy-4,5-diphenylimidazolidine-2-thiones in alcohols. Russ J Org Chem 47, 1564–1571 (2011). https://doi.org/10.1134/S1070428011100204

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