- DABCO-mediated decarboxylative cyclization of isatoic anhydride with aroyl/heteroaroyl/alkoylacetonitriles under microwave conditions: Strategy for the synthesis of substituted 4-quinolones
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An efficient, 1,4-diazabicyclo[2.2.2]octane(DABCO)-mediated decarboxylative cyclization of isatoic anhydrides with active methylene groups namely aroyl/heteroaroyl/alkoylacetonitriles under microwave condition was developed for the synthesis of substituted 4-quinolones. This method utilizes commercially available substrates, occurs under mild conditions, short reaction time, good to excellent yields, easy scale-up, and is compatible with a wide substrate scope. 4-Quinolones (3) obtained by this DABCO-mediated approach were further explored in order to evaluate their synthetic applicability. Initially, 4-quinolone derivatives were efficiently transformed into corresponding 4-Chloro-2-phenyl-quinoline-3-carbonitriles. Further, 2,4-Diphenyl-quinoline-3-carbonitriles were prepared by palladium catalyzed Suzuki-Miyaura cross-coupling of 4-Chloro-2-phenyl-quinoline-3-carbonitrile with aryl boronic acids.
- Hussain, Sahid,Rao, Mugada Sugunakara
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- One-Pot Synthesis of 4-Quinolone via Iron-Catalyzed Oxidative Coupling of Alcohol and Methyl Arene
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Herein, we describe the iron(III)-catalyzed oxidative coupling of alcohol/methyl arene with 2-amino phenyl ketone to synthesize 4-quinolone. Alcohols and methyl arenes are oxidized to the aldehyde in the presence of an iron catalyst and di-tert-butyl peroxide, followed by a tandem process, condensation with amine/Mannich-type cyclization/oxidation, to complete the 4-quinolone ring. This method tolerates various kinds of functional groups and provides a direct approach to the synthesis of 4-quinolones from less functionalized substrates.
- Lee, Seok Beom,Jang, Yoonkyung,Ahn, Jiwon,Chun, Simin,Oh, Dong-Chan,Hong, Suckchang
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p. 8382 - 8386
(2020/11/18)
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- Copper-Catalyzed Synthesis of Substituted 4-Quinolones using Water as a Benign Reaction Media: Application for the Construction of Oxolinic Acid and BQCA
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A copper-catalyzed three-component synthetic method has been developed for the synthesis of substituted 4-quinolone derivatives from substituted 3-(2-halophenyl)-3-oxopropane, aldehydes and aq. NH3 using water as an environmentally benign reaction media. Moreover, the synthetic utility of the obtained products has been successfully applied for the synthesis of available oxolinic acid and BQCA drugs. The key features of this approach include commercially available starting materials, broad scope, and moderate to good reaction yields. Reaction with formaldehyde, and other functionalities such as ?CN, ?NO2, ?SO2Ar, and ?COAr were also successful. In addition, reaction with heterocyclic compounds such as 3-(3-bromothiophen-2-yl)-3-oxopropanenitrile proceeded smoothly to afford tetrahydrothieno[3,2-b]pyridine-6-carbonitrile analogues. The practicality of the designed protocol was confirmed by gram scale synthesis of two derivatives. (Figure presented.).
- Gore, Babasaheb Sopan,Lee, Chein Chung,Lee, Jessica,Wang, Jeh-Jeng
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supporting information
(2019/05/24)
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- Switchable Access to 3-Carboxylate-4-quinolones and 1-Vinyl-3-carboxylate-4-quinolones via Oxidative Cyclization of Isatins and Alkynes
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An efficient transition-metal-free oxidative cyclization reaction using isatins and alkynes for the facile synthesis of structurally diverse 4-quinolones has been developed. Intriguingly, switchable access to substituted 3-carboxylate-4-quinolones and 1-vinyl-3-carboxylate-4-quinolones could be achieved by choosing a different base in the reaction. The obtained products could undergo further transformations, increasing the application potential of the method in organic synthesis.
- Jiang, Shi-Fen,Xu, Cheng,Zhou, Zhi-Wen,Zhang, Qin,Wen, Xiao-Hui,Jia, Feng-Cheng,Wu, An-Xin
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supporting information
p. 4231 - 4234
(2018/07/29)
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- Synthesis of fluorinated 2-phenyl-4-quinolones from pyrrole-2,3-diones
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A series of substituted 2-phenyl-4-quinolones 8-11 have been synthesized in good yields via flash vacuum thermolysis (FVT) of 1-aryl-4-cyano-5-phenylpyrrole-2,3-diones 7a-e and 1-aryl-4-methoxycarbonyl-5-phenylpyrrole-2,3-diones 7f-j. The pyrrolediones 7
- Rao, V. V. Ramana,Wentrup, Curt
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p. 1232 - 1235
(2007/10/03)
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- A Nitroketene to Nitrile Oxide Transformation
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2,3-Dihydropyrrole-2,3-diones 1 thermally extrude CO, giving imidoylketenes 2, which cyclise efficiently to 4-quinolones 3; however, the analogous nitro(imidoyl)ketene 5 eliminates CO2 and rearranges to the 3-oximino-3H-indole 9, presumably via an imidoyl
- Kappe, C. Oliver,Kollenz, Gert,Wentrup, Curt
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p. 485 - 486
(2007/10/02)
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