56409-82-6Relevant articles and documents
One-Pot Synthesis of 4-Quinolone via Iron-Catalyzed Oxidative Coupling of Alcohol and Methyl Arene
Lee, Seok Beom,Jang, Yoonkyung,Ahn, Jiwon,Chun, Simin,Oh, Dong-Chan,Hong, Suckchang
, p. 8382 - 8386 (2020/11/18)
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.
Gold-catalyzed cyclization of 1-(2′-Azidoaryl) propynols: Synthesis of polysubstituted 4-quinolones
Wu, Xiang,Zheng, Lang-Lang,Zhao, Li-Ping,Zhu, Cheng-Feng,Li, You-Gui
, p. 14769 - 14772 (2019/12/24)
An unprecedented gold-catalyzed procedure for the synthesis of polysubstituted 4-quinolones from 1-(2′-Azidoaryl) propynols is described. The reaction undergoes an intramolecular nucleophilic attack of the azide group to the Au-Activated triple bonds in a 6-endo-dig manner and subsequent gold-Assisted expulsion of N2 to furnish an α-imino gold carbene intermediate, which triggers a 1,2-carbon migration and finally is converted to 2,3-disubstituted 4-quinolone.
Microwave-assisted synthesis of polysubstituted 4-quinolones from deprotonated α-aminonitriles
Romek, Alexandra,Opatz, Till
experimental part, p. 5841 - 5849 (2011/01/04)
The α-alkylation of deprotonated N-aryl-α-aminonitriles with α-bromoesters furnishes intermediates that can be cyclized to 4-quinolones upon microwave irradiation. Alternatively, base-induced dehydrocyanation of the alkylation products furnishes enaminoes
Microwave-induced molecular rearrangements. flash thermolysis in the gas-phase and in solution: Synthesis of quinolones and naphthyridones
Lecoq, Delphine,Chalmers, Benjamin A.,Veedu, Rakesh N.,Kvaskoff, David,Bernhardt, Paul V.,Wentrup, Curt
experimental part, p. 1631 - 1638 (2010/07/04)
3- and 4-Pyridyliminopropadienones were prepared by flash vacuum thermolysis of Meldrum's acid derivatives and characterized by low temperature IR spectroscopy. They react with dimethylamine to afford 1,5-, 1,6-, and 1,7-naphthyridones. The same naphthyri
2-aryl-4-chloro-3-iodoquinolines as substrates for the synthesis of 2,3-diaryl-4-methoxyquinolines
Mphahlele, Malose J.,Mtshemla, Vathiswa
experimental part, p. 437 - 440 (2009/08/15)
Sequential functionalisation of 2-aryl-4-chloro-3-iodoquinolines via palladium-catalysed cross-coupling with phenylboronic acid followed by displacement of the 4-chloro atom from the resulting 2,3-diaryl-4- chloroquinolines with methoxide ion yielded 2,3-
Model studies related to synthesis and 1,4-dipolar cycloaddition reactions of mesoionic heterocycles
Issac, Yvette Abd El-Sayed
, p. 503 - 509 (2007/10/03)
The reaction of 2-(substituted amino)pyridine with reactive malonic acid derivatives provided an extremely facile synthesis of the mesoionic compound 4-oxo-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olates. N,N'-Disubstituted amidine reacted with diethyl malonate to afford 4-quinolone in a one-pot cyclization and rearrangement (type A/I) of 4-oxopyridiniumolate 6. The latter compound was isolated via a reaction of acyclic amidine with AME's. A cycloaddition reaction of the mesoionic pyrimidine 6 with maleic anhydride or N- phenylmaleimide yielded [2+4] cycloadducts. Triphenyl pyrrolopyridinetrione 12 was achieved via a ring transformation of the cycloadduct 4-benzyl-3,5- dioxo-1,2,6-triphenyl-2,6-diazabicyclo[2.2.2]octane-7,8-dicarboxylic anhydride 11d. In contrast, the cycloadduct 4-ethyl derivative 11c and substituted 3,5-dioxo-1,2,6-triphenyl-2,6-diazabicyclo[2.2.2]octane-7,8- dicarboxylic N-phenylimides did not give 12 under the same reaction conditions. The mechanistic pathway for the formation of 12 was studied. Dimethyl acetylenedicarboxylate reacted with 6b,c to furnish 2-oxo-1,2- dihydropyridine-4,5-dicarboxylates.
PHOTOCHEMICAL AND THERMAL REACTIONS OF HETEROCYCLES. PART 5. PRODUCTS VIA TRANSIENT QUASIANTIAROMATIC AZETINE INTERMEDIATES GENERATED BY DESULPHURISATION OF PHOTOCHEMICAL INTERMEDIATES FROM A THIAZOLIUM-4-OLATE AND 4-AMINOTHIAZOLIUM SALTS
Kato, Hiroshi,Wakao, Kozo,Yamada, Akira,Mutoh, Yasuhiro
, p. 189 - 192 (2007/10/02)
Irradiation of the mesoionic triphenylthiazolium-4-olate (3) in the presence of tributylphosphine gave the quinolinone (7).This result was interpreted as arising via desulphurisation of the bicyclic intermediate (4) to the azetone (5), followed by its isomerisation to the ketene (6) and internal trapping.Similar irradiation of the 4-aminothiazolium salts (15) gave enamino nitriles (17) and benzoylacetonitrile (16).They are probably formed by isomerisation and hydration of the hitherto unknown quasiantiaromatic 2-imino-1,2-dihydroazete intermediates (20), which in turn are generated by desulphurisation of the bicyclic photochemical intermediates (19).
