19020-26-9Relevant academic research and scientific papers
Dearomative Photocatalytic Construction of Bridged 1,3-Diazepanes
Dixon, Darren J.,Duarte, Fernanda,Leitch, Jamie A.,Rogova, Tatiana
supporting information, p. 4121 - 4130 (2020/02/05)
The construction of diverse sp3-rich skeletal ring systems is of importance to drug discovery programmes and natural product synthesis. Herein, we report the photocatalytic construction of 2,7-diazabicyclo[3.2.1]octanes (bridged 1,3-diazepanes) via a reductive diversion of the Minisci reaction. The fused tricyclic product is proposed to form via radical addition to the C4 position of 4-substituted quinoline substrates, with subsequent Hantzsch ester-promoted reduction to a dihydropyridine intermediate which undergoes in situ two-electron ring closure to form the bridged diazepane architecture. A wide scope of N-arylimine and quinoline derivatives was demonstrated and good efficiency was observed in the construction of sterically congested all-carbon quaternary centers. Computational and experimental mechanistic studies provided insights into the reaction mechanism and observed regioselectivity/diastereoselectivity.
Method for synthesizing substituted quinoline derivative 4- through palladium catalysis (by machine translation)
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Paragraph 0026-0028, (2020/01/08)
The invention belongs to the technical field of 4 - synthetic chemistry, and particularly. relates to a method for synthesizing a substituted quinoline derivative with palladium through palladium catalysis, Cs. 2 CO3 The method disclosed by, the 60-80 °C invention is 5-8 simple, and green, in 4 - synthetic process,has excellent selectivity and high yield, and has a wide substrate range, and the method has a wide, application value in the fields of pharmaceutical chemistry, biochemistry and the like. (by machine translation)
Benzylic Fluorination of Aza-Heterocycles Induced by Single-Electron Transfer to Selectfluor
Danahy, Kelley E.,Cooper, Julian C.,Van Humbeck, Jeffrey F.
supporting information, p. 5134 - 5138 (2018/03/26)
A selective and mild method for the benzylic fluorination of aromatic azaheterocycles with Selectfluor is described. These reactions take place by a previously unreported mechanism, in which electron transfer from the heterocyclic substrate to the electrophilic fluorinating agent Selectfluor eventually yields a benzylic radical, thus leading to the desired C?F bond formation. This mechanism enables high intra- and intermolecular selectivity for aza-heterocycles over other benzylic components with similar C?H bond-dissociation energies.
Pd-Catalyzed Alkylation of (Iso)quinolines and Arenes: 2-Acylpyridine Compounds as Alkylation Reagents
Wu, Qingsong,Han, Shuaijun,Ren, Xiaoxiao,Lu, Hongtao,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
supporting information, p. 6345 - 6348 (2018/10/20)
The first Pd-catalyzed alkylation of (iso)quinolines and arenes is reported. The readily available and bench-stable 2-acylpyridine compounds were used as an alkylation reagent to form the structurally versatile alkylated (iso)quinolines and arenes. The method affords a convenient pathway for the introduction of alkyl groups into organic molecules.
6-Acylamino-2-aminoquinolines as potent melanin-concentrating hormone 1 receptor antagonists. Identification, structure-activity relationship, and investigation of binding mode
Ulven, Trond,Frimurer, Thomas M.,Receveur, Jean-Marie,Little, Paul Brian,Rist, ?ystein,N?rregaard, Pia K.,H?gberg, Thomas
, p. 5684 - 5697 (2007/10/03)
Novel 6-acylamino-2-aminoquinoline melanin-concentrating hormone 1 receptor (MCH1R) antagonists were identified by sequential in silico screening with 3D pharmacophore models derived from a series of benzamide antagonists. The structure-activity relationship exploration by synthesis of analogues found structural demands around the western part of the compounds to be quite specific, whereas much structural freedom was found in the eastern part. While these compounds in general suffered from poor solubility properties, the 4-trifluoromethoxy-phenoxyacetamide western appendage provided a favorable combination of activity and solubility properties. The amine in the eastern appendage, originally required by the pharmacophore model and believed to interact with Asp123 in transmembrane 3 of MCH1R, could be removed without diminishing affinity or functional activity of the compounds. Docking studies suggested that the Asp123 interacts preferentially with the nitrogen of the central quinoline. Synthesis and testing of specific analogues supported our revised binding mode hypothesis.
O-Protecting groups as long-range stereocontrolling elements in the addition of acetylides to 4-substituted quinolines
Guanti, Giuseppe,Perrozzi, Sara,Riva, Renata
, p. 2703 - 2706 (2007/10/03)
Addition of magnesium acetylides in the presence of chloroformate esters to racemic differently O-protected 2-(4-quinolyl)propanols and to enantiopure 2-(4-quinolyl)-1,3-dialkoxypropanes, prepared by a chemoenzymatic route, gives almost exclusive regioselective attack at C-2, with stereoselectivities from moderate to good, depending mainly on the bulkiness of the O-protecting group present.
Remote control by protecting groups in the diastereoselective addition of acetylides to 2-(4-quinolyl)propanol
Guanti, Giuseppe,Perrozzi, Sara,Riva, Renata
, p. 3923 - 3927 (2007/10/03)
Differently O-protected 2-(4-quinolyl)propanols undergo, in the presence of chloroformate esters, a regio- and stereoselective addition of acetylides on the carbon α to nitrogen with moderate to good diastereoselectivity. The bulkiness of the OH protecting group, which has a 1,7 relationship with the newly created stereocentre, appears to be mainly responsible for this remote stereocontrol.
