Reaction of 1-substituted 3-aminoquinoline-2,4-diones with isothiocyanates. An easy pathway to generate novel 2-thioxo-1′<em>H</em>-spiro[imidazoline-5,3′-indole]-2,2′-diones期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

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

Affiliation:	^a Department of Chemistry, Faculty of Technology, Tomas Bata University, 762 72 Zlín, Czech Republic ^b Research Institute for Organic Syntheses (VUOS), Rybitví 296, 533 54 Pardubice 20, Czech Republic ^c University of Hradec Králové, Faculty of Education, Rokitanského 62, CZ 500 03 Hradec Králové 3, Czech Republic ^d Institute of Physiology of the Academy of Sciences of the Czech Republic, 142 20 Prague, Czech Republic ^e Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, 53210 Pardubice, Czech Republic

Abstract:	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]quinolin-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 ¹H, ¹³C, IR and MS spectra, and some of them also by ¹⁵N NMR. The structure of one compound was investigated by single-crystal X-ray diffraction.

Keywords:	α-Aminoketones Enamides Rearrangement Thiourea derivatives Spiro-heterocycles
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