10380-73-1

Upstream product

• 501-65-5 diphenyl acetylene 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 13209-38-6 (2-aminophenyl)(phenyl)methanol 
• 621-08-9 Dibenzyl sulfoxide 
• 100-52-7 benzaldehyde 
• 5176-14-7 3-phenyl-2,1-benzoxazole 
• 574-66-3 Benzophenone oxime 
• 93-98-1 N-phenyl benzoyl amide 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 58109-40-3 diphenyliodonium hexafluorophosphate 
• 100-47-0 benzonitrile 
• 451-40-1 phenyl benzyl ketone 
• 98-80-6 phenylboronic acid 
• 1859-71-8 2-(tosylamino)benzophenone 

Downstream Products

• 88795-70-4 1-Ethyl-3,4-diphenyl-1H-quinolin-2-one 

Relevant academic research and scientific papers

Amberlyst-15-catalyzed novel synthesis of quinoline derivatives in ionic liquid

In recent years, ionic liquids have attracted much attention as useful synthetic solvents. Compared with classical molecular solvents, the ionic liquids are environmentally benign reaction media. A variety of quinoline derivatives have been synthesized un

Unexpected Annulation between 2-Aminobenzyl Alcohols and Benzaldehydes in the Presence of DMSO: Regioselective Synthesis of Substituted Quinolines

An unexpected annulation among 2-aminobenzyl alcohols, benzaldehydes, and DMSO to quinolines has been disclosed. For the reported annulation between 2-aminobenzyl alcohols and benzaldehydes, the change of the solvent from toluene to DMSO led to the change of the product from the diheteroatomic cyclic benzoxazines to monoheteroatomic cyclic quinolines. This annulation can be used to synthesize regioselectively different substituted quinolines by the choice of different 2-amino alcohols, aldehydes, and sulfoxides as substrates. Interestingly, introducing substituent groups to the α-position of sulfoxides resulted in the interchange of the positions between benzaldehydes and sulfoxides in the product quinolines. On the basis of the control experiments and literatures, a plausible mechanism for this annulation was proposed.

Synthesis method for 2-position substituted polysubstituted quinoline

To the method, 2 ortho-amine aryl alcohol, aryl formaldehyde and sulfoxide are subjected to one-pot reaction in an alkali-containing toluene solution system under an oxygen-containing atmosphere, and a 1 - 2-position substituted polysubstituted quinoline

NiH-Catalyzed Hydroamination/Cyclization Cascade: Rapid Access to Quinolines

Despite the significant success of metal-H-catalyzed hydroamination methodologies, considerable limitations still exist in the selective hydroamination of alkynes, especially for terminal alkynes. Herein, we develop a highly efficient NiH catalytic system that activates readily available alkynes for a cascade hydroamination/cyclization reaction with anthranils. This mild, operationally simple protocol is amenable to a wide array of alkynes including terminal and internal, aryl and alkyl, electron-deficient and electron-rich ones, delivering structurally diverse quinolines in useful to excellent yields (>80 examples, up to 93% yield). The utility of this procedure is exhibited in the late-stage functionalization of several natural products and in the concise synthesis of an antitumor molecule graveolinine and a triplex DNA intercalator. Preliminary mechanistic experiments suggest an alkenylnickel-mediated alkyne hydroamination and an intramolecular cyclization/aromatization of putative enamine intermediates.

A Tf2O-Promoted Synthesis of Functionalized Quinolines from Ketoximes and Alkynes

A new general synthesis of quinolines was developed from ketoximes and alkynes in the presence of Tf2O. It offered the first direct synthesis of quinolines by using the nitrilium salts generated in situ from a Tf2O-promoted Beckmann rearrangement of ketoximes under very easy conditions. (Figure presented.).

Bioorganopromoted green Friedl?nder synthesis: a versatile new malic acid promoted solvent free approach to multisubstituted quinolines

The discovery of a new, malic acid promoted, eco-friendly Friedl?nder approach to varied multisubstituted quinolines is disclosed. To the best of our knowledge, this is the first report on the use of malic acid, classified as one of the 12 biobased hot molecules by the US Department of Energy, as an organopromoter in organic synthesis and includes many benefits like wide substrate scope, solvent free ambient reaction conditions, short reaction times, operational simplicity, cost effectiveness, high atom economy, good to excellent yields, and recylability of the organopromoter, making it a valuable green alternative to the existing methods. The versatility and practicability of the developed method was further established by its successful application towards the targeted synthesis of some important quinoline molecules and successful scale up.

Synthesis of Functionalized Quinolines through a Reaction of Amides and Alkynes Promoted by Triflic Anhydride/Pyridine

A concise, novel and flexible metal-free single step to synthesize functionalized quinolines is reported. Triflic anhydride-mediated (Tf2O) activation of amides is discussed in the presence of pyridine to offer strong electrophiles, thereby showcasing excellent productivity, high regio- and chemoselectivity, and widely tolerable substrates. This approach provides a straightforward and efficient way to construct azaheterocycle structures.

A pharmaceutical intermediate a method for synthesis of substituted quinoline derivatives

The invention relates to a preparation method of a medical intermediate multi-substituted quinoline derivative. High-yield preparation of a multi-substituted quinoline compound is achieved by using o-aminoaryl ketone and alkyne as raw materials and screen

Redox-Neutral Couplings between Amides and Alkynes via Cobalt(III)-Catalyzed C-H Activation

C-H activation assisted by a bifunctional directing group has allowed the construction of heterocycles. This is ideally catalyzed by earth-abundant and eco-friendly transition metals. We report Co(III)-catalyzed redox-neutral coupling between arenes and alkynes using an NH amide as an electrophilic directing group. The redox-neutral C-H activation/coupling afforded quinolines with water as the sole byproduct.

Palladium-catalyzed synthesis of polysubstituted quinolines from 2-amino aromatic ketones and alkynes

A palladium-catalyzed one-pot method for the synthesis of quinolines from commercial or readily available 2-amino aromatic ketones and alkynes is reported for the first time. This transformation offers an alternative method for the synthesis of polysubstituted quinoline. the Partner Organisations 2014.