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Molecular Rearrangement of 9b-Hydroxy-1H-imidazo[4,5-c]quinoline-2,4-diones - A Convenient Pathway to Spiro-Linked Imidazolidine-Oxindole Derivatives
Authors: Klásek Antonín | Lyčka Antonín | Mikšík Ivan | Růžička Aleš
Year: 2009
Type of publication: článek v odborném periodiku
Name of source: Helvetica Chimica Acta
Publisher name: Wiley-VCH
Place: Weinheim
Page from-to: 689-708
Titles:
Language Name Abstract Keywords
cze Molekulová studie 9b-Hydroxy-1H-imidazo[4,5-c]quinoline-2,4-diones - A convenient Pathway k Spiro-Linked Imidazolidine-Oxindolových derivátů 1- substituované 3 - alkyl/aryl-3-aminoquinoine-2,4(1H,3H)-diony 1 reagovaly s alkyl/aryl isocynáty za vzniku 3 - alkyl/aryl-3-ureidoquinoline-2,4(1H,3H)-diones (=N - - alkyl/aryl-1,2,3,4-tetrahydro-2,4-dioxoquinolin-3-yl)ureas) 2 a/nebo 3a - alkyl/aryl-3,3a,5,9b-tetrahydro-9b-hydroxy-1H-imidazo[4,5-c]quinoline -2,4 dionů 3 ve vysokých výtěžcích. Směsi 2 a 3 přecházejí vařením v AcOH nebo koncentrovaný HCl řešení na tři různé druhy spiro[imidazolidine-4,3'[3H]indole]-2,2'(1'H)-diones, i.e., 10, 11, a 12, v závislosti na druhu substituentů v C(3) a C(3a). Všechny sloučeniny byly studovány pomocí H - 1 - a C - 13 - NMR a infračervené spektroskopie a APCI hmotnostní spektrometrie. Struktury u sloučenin 11c a 12Al bylz vyřešeny rentgenovou difrakční analýzou oxindolové deriváty
eng Molecular Rearrangement of 9b-Hydroxy-1H-imidazo[4,5-c]quinoline-2,4-diones - A Convenient Pathway to Spiro-Linked Imidazolidine-Oxindole Derivatives The 1-substituted 3-alkyl/aryl-3-aminoquinoine-2,4(1H,3H)-diones 1 react with alkyl/aryl isocynates to give 3-alkyl/aryl-3-ureidoquinoline-2,4(1H,3H)-diones (=N-(3-alkyl/aryl-1,2,3,4-tetrahydro-2,4-dioxoquinolin-3-yl)ureas) 2 and/or 3a-alkyl/aryl-3,3a,5,9b-tetrahydro-9b-hydroxy-1H-imidazo[4,5-c]quinoline -2,4-diones 3 in high yields. Compounds 2 and 3 rearrange by boiling in AcOH or concentrated HCl solution to give three different types of spiro[imidazolidine-4,3'[3H]indole]-2,2'(1'H)-diones, i.e., 10, 11, and 12, depending on the kind of substituents at C(3) and C(3a), respectively. All compounds were characterized by H-1- and C-13-NMR and IR spectroscopy as well as by atmospheric-pressure chemical-ionization (APCI) mass spectra. The structures of compounds 11c and 12Al were investigated by single-crystal X-ray diffraction analysis. Oxindole Derivatives

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