α-Thioureidoalkylation of functionally substituted ureas: I. Tandem cyclization and esterification in reactions of <Emphasis Type="Italic">N</Emphasis>-(carboxyalkyl)ureas with 1,3-dialkyl-4,5-dihydroxy-4,5-diphenylimidazolidine-2-thiones in alcohols |
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| Authors: | V V Baranov G A Gazieva Yu V Nelyubina A N Kravchenko N N Makhova |
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| Institution: | 1.Zelinskii Institute of Organic Chemistry,Russian Academy of Sciences,Moscow,Russia;2.Nesmeyanov Institute of Organometallic Compounds,Russian Academy of Sciences,Moscow,Russia |
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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-thioxooctahydroimidazo4,5-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-thioxooctahydroimidazo4,5-d]imidazol-1-yl)acetate showed anxiolytic effect. |
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