- A new synthesis of naphthyridinones and quinolinones: Palladium-catalyzed amidation of o-carbonyl-substituted aryl halides
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(Equation Presented) An alternative to the Friedlander condensation for the synthesis of naphthyridinones and quinolinones has been discovered. Palladium-catalyzed amidation of halo aromatics substituted in the ortho position by a carbonyl functional group or its equivalent with primary or secondary amides leads to the formation of substituted naphthyridinones and quinolinones.
- Manley, Peter J.,Bilodeau, Mark T.
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- Environmentally benign synthesis of 4-aminoquinoline-2-ones using recyclable choline hydroxide
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Greener synthesis of 4-aminoquinoline-2-ones was achieved by intramolecular cyclization of 2-cyanophenylamide derivatives using biodegradable and recyclable choline hydroxide (ChOH). The reaction proceeds rapidly and affords the corresponding 4-aminoquinoline-2-ones with a good to excellent yield. The protocol has the advantage of easy workup, high yields, and an environmentally benign methodology compared to other reported methods. The simplicity of this method makes it an interesting alternative to other approaches.
- Sanap, Anita Kailas,Shankarling, Ganapati Subray
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p. 206 - 212
(2015/02/19)
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- Copper(I) iodide catalyzed synthesis of quinolinones via cascade reactions of 2-halobenzocarbonyls with 2-arylacetamides
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An efficient copper-catalyzed method for the synthesis of quinolinones, pyridinones, and heteroannulated pyridinones via cascade reactions of substituted 2-iodo-, 2-bromo-, and 2-chlorobenzocarbonyls with 2-arylacetamides is reported. The protocol works well for the reaction of most of the 2-iodo-, 2-bromo- and 2-chlorobenzocarbonyls with 2-arylacetamides. Georg Thieme Verlag Stuttgart · New York.
- Fu, Liangbing,Huang, Xiaoli,Wang, Deping,Zhao, Pinghua,Ding, Ke
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experimental part
p. 1547 - 1554
(2011/06/25)
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- Synthesis of Coumarins and Quinolones by Intramolecular Aldol Condensation Reactions of Titanium Enediolates
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Low-valent titanium prepared by the reduction of TiCl3 with zinc dust oxidatively adds to α-ketoamides or α-ketoesters with the formation of the corresponding titanium enediolates.These 1,2-difunctional nucleophiles, which have hardly been used in organic
- Fuerstner, Alois,Jumbam, Denis N.,Shi, Nongyuan
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p. 326 - 332
(2007/10/02)
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- Regioselective Azidation of 2,4-Dichloroquinolines
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Reactions of 2,4-dichloroquinolines (2a-f) with sodium azide in DMF lead either regioselectively to 4-azido-2-chloroquinolines (3a-f) or with excess of sodium azide and catalysts to 5-azido-tetrazoloquinolines (4a-f). 2,4-Dichloroquinolines (2g-i) having electron donating substituents in 3-position react with sodium azide in DMF to a mixture of 4-azido-2-chloroquinolines (3g-i) and 5-chlorotetrazoloquinolines (5g-i).When the reaction of the 2,4-dichloroquinolines (2a-i) with sodium azide is carried out in ethanol with addition of methanesulfonic acid, regioselectively 5-chloro-tetrazoloquinolines (5a-i) are obtained.Structural assignments of 3 and 5 have been carried out by 13C-NMR spectra, IR spectra and degradation reactions of the azido- and tetrazolo group to aminoquinolines (7 and 10) via iminophosphoranes (8 and 9).It could be shown that in 2-azido/tetrazolo-quinolines (4 and 5) the tetrazole ring structure is the dominant species.
- Steinschifter, Waltraud,Stadlbauer, Wolfgang
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p. 311 - 318
(2007/10/02)
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- A Convenient Synthesis of 11H-Indoloquinolones
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11H-Indoloquinolin-6-ones, which are containing the γ-carboline ring system, can be easily synthesized from 4-azido-3-phenyl-2(1H)-quinolones, which are obtained in a two step reaction from 4-hydroxy-3-phenyl-2(1H)-quinolones.Cyclization of the azi
- Stadlbauer, Wolfgang,Karem, Abdul-Salam,Kappe, Thomas
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- A NEW SYNTHESIS OF 4-AMINO-2-QUINOLINONES
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Addition of Grignard or organolithium reagents to N-(α-haloacyl)-N-alkylsubstituted anthranilonitriles (e.g.N-(2-bromopropionyl)-N-methyl-2-cyanoaniline)induced anion formation followed by cyclization to 4-amino-2-quinolinones (e.g. 4-amino-1,3-dimethyl-2-quinolinone (10)).Substrates lacking α-hydrogen atoms, such as N-α-bromoisobutyryl)-2-cyanoaniline, also yielded 3,3-dimethylquinolinedione (9b) by cyclization.In these cases the initial step is a halogen-metal exchange reaction.
- Bergman, Jan,Brynolf, Anna,Vuorinen, Eino
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p. 3689 - 3696
(2007/10/02)
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- Isoquinoquinolones from Phenyl Malonylheterocycles
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The reaction of 3-Phenyl-4-hydroxy-2-quinolones (1) and benzylammonium chloride yields the 4-aminocompounds 2 as main products.The isoquino-condensed quinolones 3 are formed as by-products.Thermolysis of 4-benzylamino-2-quinolones (4) affords also 3.Bette
- Stadlbauer, Wolfgang,Kappe, Thomas
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p. 751 - 760
(2007/10/02)
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