Reaction of 3-phenyl-3-aminoquinoline-2,4-diones with isothiocyanates. Facile access to novel spiro-linked 2-thioxoimidazolidine-oxindoles and imidazoline-2-thiones

3-Amino-1H,3H-chinolin-2,4-diony reagují s thiomočovinou nebo thiokyanatanem draselným ve vroucí kyselině octové za vzniku nových 2,3-dihydro-3-thioxoimidazo[1,5-c]chinazolin-5(6H)-onů nevysokých výtěžcích. Avšak, jestliže jsou výchozí látky substituovány benzylovou skupinou v poloze 3, proběhne C-debenzylace za vzniku 2,3-dihydro-2-thioxo-1H-imidazo[4,5-c]chinolin-4(5H)-onů. Podle navrženého reakčního mechanismu proběhne molekulární přesmyk původně vytvořených monosubstituovaných močovin. Všechny sloučeniny byly charakterizovány pomocí 1H, 13C, a 15N NMR, a IR spektroskopií stejně jako hmotovými spektry.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 1H, 13C, IR and MS data, and in some cases also by 15N NMR data. The structures and compositions of four compounds were confirmed by single crystal X-ray diffraction

Molecular rearrangement of 9b-hydroxy-imidazo[4,5-c]quinoline-2,4-diones ? a convenient pathway to spiro imidazolidine oxindole derivatives

3-Alkyl/Aryl-3-aminochinolin-2,4-diony reagují s isokyanáty na nové titulní sloučeniny. Tyto přesmykují varem v kyselém prostředí a poskytují tři odlišné typy spiro-oxindolů.3-Alkyl/Aryl-3-aminoquinoline-2,4-diones react with isocyanates to give novel title compounds. These compounds rearrange by boiling in acidic environment to give three different type of spiro-oxindoles

Synthesis of 2-thioxo-imidazolines via reaction of 1-unsubstituted 3-aminoquinoline-2,4-diones with isothiocyanates

3-Alkyl/Aryl-3-aminochinoline-2,4-diony reagují s isothiokyanáty za tvorby 3a-alkyl/aryl-1,2,3,3a-tetrahydro-9b-hydroxy-2-thioxo-5H-imidazo-[4,5-c]chinolin-4(9bH)-onů. Tyto sloučeniny přesmykují v kyselém prostředí na nové 4-(2-aminofenyl)-1H-imidazol-2(3H)-thiony a 1,3-bis(2-(2,3-dihydro-2-thioxo-1H-imidazol-5-yl)fenyl)močoviny.3-Alkyl/Aryl-3-aminoquinoline-2,4-diones react with isothiocyanates to give 3a-alkyl/aryl-1,2,3,3a-tetrahydro-9b-hydroxy-2-thioxo-5H-imidazo-[4,5-c]quinolin-4(9bH)-ones. These compounds rearrange in an acidit environment to give novel 4-(2-aminophenyl)-1H-imidazole-2(3H)-thiones and 1,3-bis(2-(2,3-dihydro-2-thioxo-1H-imidazol-5-yl)phenyl)ureas

Reaction of 1-substituted 3-aminoquinoline-2,4-diones with isothiocyanates. An easy pathway to generate novel 2-thioxo-10H-spiro[imidazoline-5,3-indole]-2,2´-diones.

3-Butyl-3-aminochinolin-2,4-diony reagují s isothiokyanáty za tvorby nových 3a-butyl-9b-hydroxy-hexahydro-imidazo[4,5-c]chinolin-2-onů. Tyto sloučeniny přesmykují v kyselém prostředí a poskytují (E)- a/nebo (Z)-4-butyliden-2-thioxo-1´H-spiro[imidazolin-5,3´-indol]-2,2-diony.3-Butyl-3-aminoquinoline-2,4-diones react with isothiocyanates to give novel 3a-butyl-9b-hydroxy-hexahydro-imidazo[4,5-c]quinolin-2-ones . These compounds rearrange in an acidit environment to give (E)- and/or (Z)-4-butylidene-2-thioxo-1´H-spiro[imidazoline-5,3´-indole]-2,2-diones

Quinolone based chemosensor for the naked-eye and spectrophotometric detection of Cu2+in aqueous media

A new 4-hydroxy-2-quinolone based chemosensor (BPHTQ-1) was designed for the spectrophotometric and naked-eye detection of Cu2+. The chemosensor displayed a high selectivity and sensitivity towards Cu2+in the presence of other competitive metal cations in pure aqueous media. The Cu2+recognition furnished a distinguishable color change of BPHTQ-1 from colorless to yellow with a significant hyperchromic shift at 300 nm. The S and O atoms of BPHTQ-1 provided a 1:1 binding scaffold for the recognition of Cu2+ion with a high binding affinity of 19,338 M- 1and a detection limit of 1.39 μM, which is quite low compared with World Health Organization (WHO) reports.DST, New Delhi, India; Ministerio de Economia y Competitividad (Spain)/FEDER (EU) [BFU2011-30161-C02-02