61707-51-5Relevant academic research and scientific papers
Pd-NHC catalysed Carbonylative Suzuki coupling reaction and its application towards the synthesis of biologically active 3-aroylquinolin-4 (1H)-one and acridone scaffolds
Ghosh, Prasanjit,Ganguly, Bhaskar,Das, Sajal
, (2018/03/01)
We have unfolded a convenient and mild protocol for the synthesis of diaryl ketones via Pd- NHC catalysed carbonylative Suzuki coupling reaction. Notably, this method offers advantages like no use of toxic CO gas, shorter reaction time, high yield, and broad substrate scope. Several sensitive functional groups (like-COMe, -COOMe, -F, -Cl, -Br, -NH2, -CN) are well tolerated in this reaction. In addition, we have also demonstrated a new efficient route for the synthesis of biologically active and pharmaceutically important 2-substituted 3-Aroylquinolin-4(1H)-ones and acridone scaffolds.
Design, Palladium-Catalyzed Synthesis, and Biological Investigation of 2-Substituted 3-Aroylquinolin-4(1H)-ones as Inhibitors of the Hedgehog Signaling Pathway
Alfonsi, Romina,Botta, Bruno,Cacchi, Sandro,Di Marcotullio, Lucia,Fabrizi, Giancarlo,Faedda, Roberta,Goggiamani, Antonella,Iazzetti, Antonia,Mori, Mattia
, p. 1469 - 1477 (2017/03/08)
2-Substituted 3-aroylquinolin-4(1H)-ones, prepared through a palladium-catalyzed carbonylative cyclization of N-(2-iodoaryl)enaminones, proved to inhibit efficiently the Hedgehog pathway through direct antagonism of the wild-type and drug-resistant form o
The Reactions of Some ortho-Substituted Anilines With Various α,β-Acetylenic Ketones. A Route to Substituted Quinolines
Sinsky, M. S.,Bass, R. G.
, p. 759 - 768 (2007/10/02)
The reactions of some ortho-substituted anilines with various α,β-acetylenic ketones were investigated as a route to 4-alkyl-, 4-aryl-, 4-hydroxy-, and 4-amino-3-quinolyl ketones.The anilines examined were 2-aminoacetophenone (1), 2-aminobenzophenone (2), anthranilonitrile (3), methyl anthranilate (4), and ethyl anthranilate (5).The acetylenic ketones used were 1,4-diphenyl-2-butyne-1,4-dione (6), 3-butyn-2-one (7), 1,3-diphenyl-2-propyn-1-one (8), and 4-phenyl-3-butyn-2-one (9).The acetylenic ketones typically reacted with the anilines to give enamines; however, exceptions were found.Acetylene 6 reacts with 3 to give the enamine (13) along with a small amount of 2,3-dibenzoyl-4-quinolamine (14).The reactions of 1 or 2 with 6 give the respective quinoline derivatives directly.Acetylene 8 reacts with 2 to give 3-benzoyl-2,4-diphenylquinoline (22) directly, whereas no reaction occurs between 8 and 1 or 3.Acetylene 9 does not react with 1, 2 or 3.The enamines exist as the intramolecularly hydrogen bonded isomers and usually undergo cyclization with 5 molar equivalents of methanolic sodium methoxide to give quinoline derivatives.The 4-quinolinols exist predominantly as the 4-quinolinone tautomer.
Reactions of Cyclic Oxalyl Compounds, XXIII. Reactions of Five-membered 2,3-Dioxo Heterocycles with Carbodiimides - a Synthetic Pathway to Hetero Analogues of Deazapurine Systems
Kollenz, Gert,Penn, Gerhard,Ott, Walter,Peters, Karl,Peters, Eva-Maria,et al.
, p. 1310 - 1329 (2007/10/02)
The furandione 1 reacts with diaryl- or arylalkylcarbodiimides to yield 4--2,3-furandiones 5, which isomerize to 2,3-pyrrolediones 2 above 60 deg C. 1, 2, and 5 react with dimethylcarbodiimide under mild conditions (20 deg C, a few minutes) to give the so far unknown pyrrolooxazinediones 7 which reversibly can lose dimethylcarbodiimide to form again 2.Analogously 2,3-thiophenedione 3 and dimethyl- or diisopropylcarbodiimide yield the pyrrolothiazines 8.The basic skeletons of 7 and 8 were determined by X-ray structure analys is of 7a and 8b.On the other hand, the reaction of 1 with diethyl- or diisopropylcarbodiimide leads to furopyrimidines 10.The bicyclic compounds 7, 8, and 10 can be regarded as heteroanalogues of the 7-deazapurine system.The reaction pathways leading to 5, 7, 8, and 10 involve cycloadditions, cycloreversions or fragmentation reactions as well as some surprising new furandione-furandione rearrangements.
