- Direct amination of nitroquinoline derivatives via nucleophilic displacement of aromatic hydrogen
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The vicarious nucleophilic substitution of hydrogen (VNS) reaction in electron-deficient nitroquinolines was studied. Properties of all new products have been characterized by several techniques: MS, HRMS, FTIR, GC-MS, electronic absorption spectroscopy, and multinuclear NMR. The structures of 4-chloro-8-nitroquinoline, 8-(tert-butyl)-2-methyl-5-nitroquinoline, 9-(8nitroquinolin-7-yl)-9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one were determined by single-crystal X-ray diffraction measurements. The 9-(8-nitroquinolin-7-yl)9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one illustrate the nitro/nitroso conversion within VNS reaction. Additionally, 9-(8-isopropyl-2-((8-isopropyl-2-methyl5-nitroquinolin-6-yl)methyl)-5-nitrosoquinolin-6-yl)-9H-carbazole is presented as a double VNS product. It is postulated that the potassium counterion interacts with the oxygen on the nitro group, which could influence nucleophile attack in that way.
- Ksi??ek, Maria,Kubí?ek, Vladimír,Kusz, Joachim,Ma?ecki, Jan Grzegorz,Nycz, Jacek E.,Swoboda, Daniel,Wantulok, Jakub
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- Direct C-3-alkenylation of quinolones via palladium-catalyzed C-H functionalization
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An unprecedented C-3-alkenylation of quinolones was reported through palladium-catalyzed C-H functionalization with 1% catalyst loading. This method provides an efficient route to a variety of new quinolone derivatives.
- Li, Mingzong,Li, Liangxi,Ge, Haibo
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supporting information; experimental part
p. 2445 - 2449
(2010/12/25)
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- Synthesis and biological evaluation of new heterocyclic quinolinones as anti-parasite and anti-HIV drug candidates
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We have synthesized quinolinones with potential antiparasitic and anti-HIV activities by an original two-step method involving microwave irradiation and have evaluated their activities against Plasmodium falciparum, Leishmania donovani, Trichomonas vaginalis, and HIV. None of the tested compounds had been previously described using this method of synthesis. One of the compounds had interesting antiparasitic and anti-HIV activity, which could be improved by substitution with different radicals.
- Darque, Albert,Dumetre, Aurelien,Hutter, Sebastien,Casano, Gilles,Robin, Maxime,Pannecouque, Christophe,Azas, Nadine
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supporting information; experimental part
p. 5962 - 5964
(2010/06/17)
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- Regioselective synthesis of quinolin-4-ones by pyrolysis of anilinomethylene derivatives of Meldrum's acid
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Electron-rich and electron-deficient anilinomethylene derivatives of Meldrum's acid cyclize equally efficiently to quinolin-4-ones via imidoylketene intermediates under flash vacuum pyrolysis (FVP) conditions. Georg Thieme Verlag Stuttgart.
- Hill, Lawrence,Imam, S. Haider,McNab, Hamish,O'Neill, William J.
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experimental part
p. 1847 - 1851
(2009/12/05)
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- Gas-phase pyrolysis in organic synthesis: Rapid green synthesis of 4-quinolinones
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Gas-phase pyrolysis of aminomethylene Meldrum's acid derivatives gave quinolinones and/or amines depending on the nature of arylamino moiety. Effect of substituent on reaction rate and nature of pyrolysis products supports the suggested intramolecular nucleophilic substitution reaction via initially formed keteneamine intermediate. Georg Thieme Verlag Stuttgart.
- Al-Awadi, Nouria A.,Abdelhamid, Ismail Abdelshafy,Al-Etaibi, Alya M.,Elnagdi, Mohamed Hilmy
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p. 2205 - 2208
(2008/02/10)
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- Exotic amino acids. 8. Synthesis of monomethyl esters of N-aryl-aminomethylenemalonic acids
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N-Arylaminomethyleneisopropylidenemalonates, obtained from ethoxymethyleneisopropylidenemalonate and aromatic amines, underwent methanolysis to form monomethyl esters of N-arylaminomethylenemalonic acids. The conditions of their formation and their yields depend on the nature and positions of the substituents in the aromatic ring of the initial amine.
- Zicane,Ravina,Tetere,Rijkure,Petrova,Kalejs
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p. 840 - 845
(2007/10/03)
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- SYNTHESIS OF 4(1H)-QUINOLONES BY THERMOLYSIS OF ARYLAMINOMETHYLENE MELDRUM'S ACID DERIVATIVES
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A series of 4(1H)-quinolones were obtained from Meldrum's acid and arylamines in two steps.
- Cassis, Raul,Tapia, Ricardo,Valderrama, Jaime A.
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p. 125 - 134
(2007/10/02)
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