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Reaction of 3-phenyl-3-aminoquinoline-2,4-diones with Isothiocyanates. Facile Access to Novel Spiro-linked 2-thioxoimid-azolidine-oxindoles and Imidazoline-2-thiones
Authors: Klásek Antonín | Lyčka Antonín | Mikšík Ivan | Růžička Aleš
Year: 2010
Type of publication: článek v odborném periodiku
Name of source: Tetrahedron
Publisher name: Pergamon-Elsevier Science Ltd.
Place: Oxford
Page from-to: 2015-2025
Titles:
Language Name Abstract Keywords
cze Reakce 3-fenyl-3-aminochinolin-2,4-dionu s Isothiocyanaty. Jednoduchý přístup k novým 2-thioxoimid-azolidin-oxindolům a imidazolin-2-thionům 3-fenyl-3-amino-1H,3H-chinolin-2,4-dion (1) reaguje s alkyl nebo aryl isothiocyanáty za vzniku 9b-hydroxy-3a-fenyl-1,2,3,3a-tetrahydro-2-thioxo-5H-imidazo[4,5-c]chinolin-4(9bH)-onů. Tyto sloučeniny se přeskupují v horké kyselině octové nebo koncentrované kyselině chlorovodíkové ne 5-fenyl-2-thioxospiro[4H-imidazol-4,3'-[3H]indol]-2'(1'H,3H)-onát, 5-hydroxy-5-fenyl-2-thioxospiro [imidazolidine-4,3'-[3H]indol]-2'-ony a (2-methylaminofenyl)-5-fenyl-1H-imidazol-2(3H)-thiony. U všech sloučenin byly určeny H-1, C-13, IR a MS data, a v některých případech také N-15 NMR. Struktury od čtyř sloučenin byly potvrzeny rentgenovou difrakcí. alfa aminoketony, spiro heterocykly, thioxo skupina, thiomočovinové deriváty
eng Reaction of 3-phenyl-3-aminoquinoline-2,4-diones with Isothiocyanates. Facile Access to Novel Spiro-linked 2-thioxoimid-azolidine-oxindoles and Imidazoline-2-thiones 3-Phenyl-3-amino-1H,3H-quinoline-2,4-diones (1) react with alkyl or aryl isothiocyanates to give novel 9b-hydroxy-3a-phenyl-1,2,3,3a-tetrahydro-2-thioxo-5H-imidazo[4,5-c]quinolin-4(9bH)-ones in high yields. These compounds rearrange in boiling acetic acid or concentrated hydrochloric acid to give novel 5-phenyl-2-thioxospiro[4H-imidazol-4,3'-[3H]indol]-2'(1'H,3H)-ones, 5-hydroxy-5-phenyl-2-thioxospiro [imidazolidine-4,3'-[3H]indol]-2'-ones and (2-methylaminophenyl)-5-phenyl-1H-imidazole-2(3H)-thiones. All compounds were characterized by their H-1, C-13, IR and MS data, and in some cases also by N-15 NMR data. The structures and compositions of four compounds were confirmed by single crystal X-ray diffraction. (C) 2010 Elsevier Ltd. All rights reserved alpha-Aminoketones; Rearrangement; Spiro-heterocycles; Thioxo group; Thiourea derivatives

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