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Reaction of 1-substituted 3-aminoquinoline-2,4-diones with isothiocyanates. An easy pathway to generate novel 2-thioxo-1 'H-spiro[imidazoline-5,3 '-indole]-2,2 '-diones
Authors: Klásek Antonín | Mrkvička Vladimír | Lyčka Antonín | Mikšík Ivan | Růžička Aleš
Year: 2009
Type of publication: článek v odborném periodiku
Name of source: Tetrahedron
Publisher name: Pergamon-Elsevier Science Ltd.
Place: Oxford
Page from-to: 4908-4916
Titles:
Language Name Abstract Keywords
cze Reakce 1-substituted 3-aminoquinoline-2,4-diones s isothiocyanáty. A snadnější příprava 2-thioxo-1 ' H-spiro[imidazoline-5,3 '-indole]-2,2 '-diones 3 - Butyl - 3 -amino-1H,3H-quinoline-2.4-diones reaguje s isothiocyanáty za vzniku 3a - butyl - 9b-hydroxy-2-thioxo-1,2,3,3a,5,9b-hexahydro-imidazo[4,5-c]quino liny- 2- jeden ve vysokých výtěžcích. Tyto sloučeniny přecházejí ve vroucí kyselině octové nebo koncentrované kyselině chlorovodíkové na (E) - a/nebo (Z) - 4 - butylidene-2-thioxo-1'H-spiro[imidazoline-5,3'-indole]-2,2'-diones. Všechny sloučeninz byly charakterizovány z jejich H- 1, C- 13, IR a MS spekter, a některéí z nich také z N - 15 NMR. Struktura jednohé sloučeniny byla vyřešena rentgenovou difrakcí 3-aminoquinolin-2,4-diony
eng Reaction of 1-substituted 3-aminoquinoline-2,4-diones with isothiocyanates. An easy pathway to generate novel 2-thioxo-1 'H-spiro[imidazoline-5,3 '-indole]-2,2 '-diones 3-Butyl-3-amino-1H,3H-quinoline-2.4-diones react with isothiocyanates to give novel 3a-butyl-9b-hydroxy-2-thioxo-1,2,3,3a,5,9b-hexahydro-imidazo[4,5-c]quino lin-2-ones in high yields. These compounds rearrange in boiling acetic acid or concd hydrochloric acid to give (E)- and/or (Z)-4-butylidene-2-thioxo-1'H-spiro[imidazoline-5,3'-indole]-2,2'-diones. All compounds were characterized by their H-1, C-13, IR and MS spectra, and some of them also by N-15 NMR. The structure of one compound was investigated by single-crystal X-ray diffraction. 3-aminoquinoline-2,4-diones

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