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Upstream product

• 1561153-03-4 3-methyl-2-(methylthio)-4-phenylquinoline 
• 103-72-0 phenyl isothiocyanate 
• 673-32-5 1-Phenylprop-1-yne 
• 622-79-7 benzyl azide 
• 63136-60-7 4-chloro-3-methylquinoline 
• 98-80-6 phenylboronic acid 
• 75-08-1 ethanethiol 
• 536-74-3 phenylacetylene 
• 62-53-3 aniline 
• 412339-09-4 2-(1-phenylprop-1-en-1-yl)aniline 
• 67-68-5 dimethyl sulfoxide 
• 64097-92-3 2-(1-phenylvinyl)aniline 
• 72349-31-6 (2-(allylamino)phenyl)(phenyl)methanone 
• 100-39-0 benzyl bromide 

Relevant academic research and scientific papers

Base-Catalyzed Cascade Reaction of ortho-(Propargylamino)aryl Ketones with N-, O-, or S-Based Nucleophiles for the Synthesis of 3-Functionalized Quinoline Scaffolds

A metal-free and base-catalyzed cascade reaction of ortho-(propargylamino)aryl ketones with primary alcohols, secondary amines, including various N-heterocycles, and thiols through 1,4-benzoxazepine intermediates was developed, providing a series of synth

Design of Benzimidazolyl Phosphines Bearing AlterableP,OorP,N-Coordination: Synthesis, Characterization, and Insights into Their Reactivity

A new series of hemilabile benzimidazolyl phosphines is reported. Entities in this ligand family can be easily assembled and prepared on a large scale via a simple one-pot procedure. X-ray crystallographic analyses show that the Pd metal center can coordinate in different fashions, where it relies on the size of the ?PR2group. With the same ligand scaffold, the ligand having a ?PCy2moiety displays better efficiency in expediting aromatic C-C bond-coupling reactions, while the ligand associated with a ?P-t-Bu2group, in contrast, promotes C-N bond-forming reactions.

DMSO/t-BuONa/O2-Mediated Aerobic Dehydrogenation of Saturated N-Heterocycles

Aromatic N-heterocycles such as quinolines, isoquinolines, and indolines are synthesized via sodium tert-butoxide-promoted oxidative dehydrogenation of the saturated heterocycles in DMSO solution. This reaction proceeds under mild reaction conditions and has a good functional group tolerance. Mechanistic studies suggest a radical pathway involving hydrogen abstraction of dimsyl radicals from the N-H bond or α-C-H of the substrates and subsequent oxidation of the nitrogen or α-aminoalkyl radicals.

Carbon annulation of ortho-vinylanilines with dimethyl sulfoxide to access 4-aryl quinolines

A palladium-catalyzed annulation of ortho-vinylanilines with dimethyl sulfoxide was developed to access 4-aryl quinolines in moderate to good yields. Activated by 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), DMSO served as a “=CH-” fragment in this transformation. It represents a facile pathway leading to 4-aryl quinolines.

Concise Synthesis of 4-Arylquinolines via Intramolecular Cyclization of Allylamines and Ketones

The intramolecular cyclization of allylamines and ketones was achieved in the presence of potassium tert-butoxide and N,N-dimethylformamide. A series of 4-arylquinolines was prepared in good yields. The reaction could be accomplished at room temperature using only a substoichiometric amount of potassium tert-butoxide. On the other hand, the reaction of the structurally analogous allyl ethers afforded diverse products. The reaction may proceed via the rearrangement of α-aminoallyl radicals and the generation of nucleophilic enamine intermediates. This finding represents a new strategy for the synthesis of quinoline derivatives from readily available 2-(allylamino)phenyl ketones.

Metal-free aerobic one-pot synthesis of substituted/annulated quinolines from alcohols via indirect Friedl?nder annulation

Metal-free, operationally simple, and highly efficient one-pot aerobic process for the synthesis of functionalized/annulated quinolines is devised from easily available 2-aminobenzyl alcohol/2-aminobenzophenones and alkyl/aryl alcohols for the first time. The process involves two sequential reactions, namely in situ aerial oxidation of alcohols to the corresponding aldehydes/ketones followed by Friedl?nder annulation.

Copper promoted synthesis of substituted quinolines from benzylic azides and alkynes

A novel copper promoted synthesis of substituted quinolines from various benzylic azides and internal alkynes has been demonstrated. The reaction features a broad substrate scope, high product yields and excellent regioselectivity. In contrast to the known two-step process of acid promoted [4 + 2] cycloaddition reaction and oxidation, the present methodology allows the synthesis of quinolines in a single step under neutral reaction conditions and can be applied to the synthesis of biologically active 6-chloro-2,3-dimethyl-4-phenylquinoline (antiparasitic agent) and 3,4-diphenylquinolin-2(1H)-one (p38αMAP kinase inhibitor). A plausible reaction mechanism involves rearrangement of benzylic azide to N-arylimine (Schmidt reaction) followed by intermolecular [4 + 2] cycloaddition with internal alkynes.

Modular o-quinone catalyst system for dehydrogenation of tetrahydroquinolines under ambient conditions

Quinolines are common pharmacophores present in numerous FDA-approved pharmaceuticals and other bioactive compounds. Here, we report the design and development of new o-quinone-based catalysts for the oxidative dehydrogenation of tetrahydroquinolines to afford quinolines. Use of a Co(salophen) cocatalyst allows the reaction to proceed efficiently with ambient air at room temperature. The utility of the catalytic method is demonstrated in the preparation of a number of medicinally relevant quinolines.

Alkyltriflate-triggered annulation of arylisothiocyanates and alkynes leading to multiply substituted quinolines through domino electrophilic activation

The reaction of arylisothiocyanate, alkyltriflate, and alkynes leads to variously substituted quinolines in high yields. The reaction undergoes alkyltriflate-triggered domino electrophilic activation and avoids the use of a transition-metal catalyst. A variety of functional groups are tolerated in the quinoline ring.

Flash Vacuum Thermolysis of 5-Substituted-4,4-diphenyl-3-oxa-1-azabicyclohexan-2-ones. A New Route to Quinolines.

Thermolysis of bicyclic carbamates produces quinoline derivatives in good yields.A two step reaction is described. Key Words: Flash vacuum thermolysis; 5-substituted-4,4-diphenyl-3-oxa-1-azabicyclohexan-2-ones; quinolines.