601520-23-4Relevant academic research and scientific papers
Reaction of 1-substituted 3-aminoquinolinediones with isocyanic and isothiocyanic acid
Mrkvi?ka, Vladimír,Rudolf, Ond?ej,Ly?ka, Antonín,Klásek, Antonín
experimental part, p. 2407 - 2413 (2011/05/05)
1-Substituted-3-aminoquinoline-2,4(1H,3H)-diones react with potassium cyanate or potassium thiocyanate in boiling acetic acid to give ureido- or thioureidooxindoles, spiro-oxindoles and dihydroimidazoquinolones. However, if the starting compounds are subs
Molecular rearrangement of 1-substituted 3-aminoquinoline-2,4-diones in their reaction with urea and nitrourea synthesis and transformations of reaction intermediates
Klasek, Antonin,Lyoka, Antonin,Holcapek, Michal,Kovar, Michal,Hoza, Ignac
, p. 1251 - 1260 (2007/10/03)
1-Substituted 3-alkyl/aryl-3-amino-1H,3H-quinoline-2,4-diones (6) react with nitrourea to give 3-ureido-1H,3H-quinoline-2,4-diones (10), 9b-hydroxy-3,3a,5,9b-tetrahydro-1H-imidazo[4,5-c]quinoline-2,4-diones (11), and 3,3a-dihydro-5H-imidazo[4,5-c]quinoline-2,4-diones (12). Compounds 11 were dehydrated to 12 by the action of phosphorus pentoxide. All three types of compounds rearrange in boiling acetic acid to give three different types of products of molecular rearrangement. A proposed reaction mechanism is discussed.
Reaction of 1-alkyl/aryl-3-amino-1H,3H-quinoline-2,4-diones with urea. Synthetic route to novel 3-(3-acylureido)-2,3-dihydro-1H-indol-2-ones, 4-alkylidene-1′H-spiro[imidazolidine-5,3′-indole]-2,2′- diones, and 3,3a-dihydro-5H-imidazo[4,5-c]quinoline-2,4-diones
Klásek, Antonín,Ko?istek, Kamil,Ly?ka, Antonín,Hol?apek, Michal
, p. 5279 - 5288 (2007/10/03)
1-Substituted 3-alkyl/aryl-3-amino-1H,3H-quinoline-2,4-diones react with urea in boiling acetic acid to give products depending on the type of substitution in position 3 and at the nitrogen atom of the 3-amino group. Starting compounds bearing a primary amino group in position 3 give 3-(3-acylureido)-2,3-dihydro-1H-indol-2-ones. Starting compounds bearing a secondary amino group in position 3 react according to the character of the other substituent in position 3. If there is a hydrogen atom α to the carbon atom C(3), 4-alkylidene-1′H-spiro[imidazolidine-5,3′-indole]-2,2′- diones arise. If a hydrogen atom is not present in this position, the reaction leads to 3,3a-dihydro-5H-imidazo[4,5-c]quinoline-2,4-diones. Reaction mechanisms for these transformations are proposed. All compounds were characterized by their 1H, 13C, IR and atmospheric pressure chemical ionization mass spectra and some of them also by 15N NMR data.
