24220-92-6Relevant academic research and scientific papers
Cu(I)-Catalyzed Alkynylation of Quinolones
Maestro, Aitor,Lemaire, Sebastien,Harutyunyan, Syuzanna R.
, p. 1228 - 1231 (2022/02/14)
Herein we report the first alkynylation of quinolones with terminal alkynes under mild reaction conditions. The reaction is catalyzed by Cu(I) salts in the presence of a Lewis acid, which is essential for the reactivity of the system. The enantioselective version of this transformation has also been explored, and the methodology has been applied in the synthesis of the enantioenriched tetrahydroquinoline alkaloid cuspareine.
Iodine/persulfate-promoted site-selective direct thiolation of quinolones and uracils
Beukeaw, Danupat,Noikham, Medena,Yotphan, Sirilata
supporting information, (2019/09/03)
A simple and general method for direct thiolation of 4-quinolones with disulfides or thiols under I2/K2S2O8 system has been developed. Under the optimal conditions, the C–S bond coupling can take place effectively with good to decent yields and excellent regioselectivity of the S-linked products. The established metal-free site-selective approach was also applicable to transform a range of uracil substrates to the thio-substituted products under mild conditions. Further transformation to the sulfone derivatives can be conveniently performed in one-pot. These easy-to-handle protocols represent a useful and interesting synthetic alternative with good substrate scope and functional group compatibility.
Highly Enantioselective Catalytic Addition of Grignard Reagents to N-Heterocyclic Acceptors
Guo, Yafei,Harutyunyan, Syuzanna R.
supporting information, p. 12950 - 12954 (2019/08/07)
General methods to prepare chiral N-heterocyclic molecular scaffolds are greatly sought after because of their significance in medicinal chemistry. Described here is the first general catalytic methodology to access a wide variety of chiral 2- and 4-substituted tetrahydro-quinolones, dihydro-4-pyridones, and piperidones with excellent yields and enantioselectivities, utilizing a single catalyst system.
Iridium(III)-Catalyzed Regiocontrolled Direct Amidation of Isoquinolones and Pyridones
Das, Debapratim,Samanta, Rajarshi
supporting information, p. 379 - 384 (2017/12/26)
Iridium(III)-catalyzed highly regiocontrolled C3/C8 amidation of isoquinolones and C6 amidation of 2-pyridones has been successfully accomplished with various azides. The optimized method is operationally simple with a broad substrate scope. The protocol has been found to be scalable. (Figure presented.).
Selectivity of N-versus O-alkylation in Mitsunobu reactions with various quinolinols and isoquinolinols
Hartung, Ryan E.,Wall, Mark C.,Lebreton, Sylvain,Smrcina, Martin,Patek, Marcel
, p. 1305 - 1313 (2017/07/18)
Reacting quinolinols and isoquinolinols under Mitsunobu conditions can give rise to N-alkylated products in addition to the normally desired O-alkylated structures. An in-depth study of how the solvent, reagent equivalents, position of the quinoline/isoqu
Synthesis of bridged benzazocines and benzoxocines by a titanium-catalyzed double-reductive umpolung strategy
Bichovski, Plamen,Haas, Thomas M.,Kratzert, Daniel,Streuff, Jan
supporting information, p. 2339 - 2342 (2015/02/05)
A sequence of two titanium(III)-catalyzed reductive umpolung reactions is reported that allows the rapid construction of benzazo- and benzoxozine building blocks. The first step is a reductive cross-coupling of quinolones or chromones with Michael acceptors. This reaction proceeds with complete syn-selectivity for the quinolone functionalization while the anti-diastereomers are obtained as the major products from chromones. With different reaction conditions, the stereochemical outcome can be altered to afford the syn-chromanone products as well. A subsequent reductive ketyl radical cyclization forges the tricyclic title compounds in good yields. A stereochemical model explaining the observed stereoselectivities is provided and the product configurations were unambiguously verified by X-ray analyses and 2D NMR spectroscopic experiments.
A copper-mediated cross-coupling approach for the synthesis of 3-heteroaryl quinolone and related analogues
Shin, Sanghye,Kim, Yechan,Kim, Kiho,Hong, Sungwoo
supporting information, p. 5719 - 5726 (2014/07/22)
An efficient and practical method for the direct cross-coupling between quinolones and a range of azoles was developed via copper-mediated C-H functionalization. This synthetic strategy provides a convenient access to a variety of C3-heteroaryl quinolones
Synthesis of 4-quinolones through nickel-catalyzed intramolecular amination on the β-carbon of o-(N-alkylamino)propiophenones
Ueno, Satoshi,Shimizu, Ryosuke,Maeda, Ryohei,Kuwano, Ryoichi
supporting information; experimental part, p. 1639 - 1642 (2012/07/17)
o-(N-Alkylamino)propiophenones are converted into 4-quinolones in the presence of chlorobenzene, potassium phosphate, morpholine, and nickel(0) catalyst. The reaction proceeds through the nickel-catalyzed formation of β-enaminones from o-(N-alkylamino)propiophenones and morpholine, followed by the intramolecular transamination. Georg Thieme Verlag Stuttgart · New York.
Direct C-3-alkenylation of quinolones via palladium-catalyzed C-H functionalization
Li, Mingzong,Li, Liangxi,Ge, Haibo
supporting information; experimental part, p. 2445 - 2449 (2010/12/25)
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.
The Oxidation of 1-Alkyl(aryl)quinolinium Chlorides with Rabbit Liver Aldehyde Oxidase
Angelino, S. A. F. G.,Valkengoed, B. H. van,Buurman, D. J.,Plas, H. C. van der,Mueller, F.
, p. 107 - 112 (2007/10/02)
1-Alkyl(aryl)quinolinium chlorides are oxidized by rabbit liver aldehyde oxidase at positions C-2 and C-4.The site and the maximum rate of oxidation are dependent on the size and the steric conformation of the N-1 substituent.The presence of a 3-carboxamido group directs the oxidation completely to position C-4, irrespective of the size of the N-substituent.Application of covalent amination in liquid ammonia as an "enzyme model" for the oxidation of these compounds shows little resemblance.
