265990-67-8

Upstream product

• 17418-09-6 4-hydroxy-4-(2-nitrophenyl)butan-2-one 
• 115698-86-7 4-(2-nitrophenyl)but-3-en-2-one 
• 552-89-6 2-nitro-benzaldehyde 
• 20766-40-9 (E)-4-(2-nitrophenyl)but-3-en-2-one 
• 529-23-7 o-aminobenzaldehyde 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 

Downstream Products

• 91-63-4 2-methylquinoline 
• 1266349-74-9 (E)-4-(2-(((E)-benzylidene)amino)phenyl)but-3-en-2-one 
• 1234713-42-8 1-(2-phenyl-1H-indol-3-yl)propan-2-one 
• 1780-19-4 (R)-1,2,3,4-tetrahydroquinaldine 
• 200125-70-8 (S)-2-methyl-1,2,3,4-tetrahydroquinoline 

Relevant academic research and scientific papers

Continuous Flow Synthesis of Quinolines via a Scalable Tandem Photoisomerization-Cyclization Process

A continuous photochemical process is presented that renders a series of quinoline products via an alkene isomerization and cyclocondensation cascade. It is demonstrated that a high-power LED lamp generates the desired targets with higher productivity and efficiency than a medium-pressure Hg-lamp. The scope of this tandem process is established and allows for the generation of various substituted quinolines in high yields and with throughputs of greater than one gram per hour. Finally, this effective flow process is coupled with a telescoped hydrogenation reaction to render a series of tetrahydroquinolines including the antimalarial natural product galipinine.

Visible-light driven synthesis of polycyclic benzo[: D] [1,3]oxazocine from 2-aminochalcone

Herein, we report a tandem cycloisomerization/nucleophilic addition/cyclization of 2-amino chalcone with bifunctional nucleophiles driven by visible light. This cascade process is realized by the irradiation of a blue LED at room temperature, which provides a concise route to structurally diverse benzo[d][1,3]oxazocine scaffolds. Mechanistic studies show that the reaction is initiated with the E to Z isomerization of a C-C double bond upon the irradiation of visible light, followed by cyclization/rearomatization to generate a transient quinolinium intermediate, which is trapped by the nucleophile and cyclized to produce the polycyclic benzo[d][1,3]oxazocine.

Enantioselective Synthesis of Tetrahydroquinolines via One-Pot Cascade Biomimetic Reduction?

A novel and efficient protocol for the synthesis of chiral tetrahydroquinoline derivatives with excellent enantioselectivities and high yields has been developed through one-pot cascade biomimetic reduction. The detailed reaction pathway includes the acid-catalyzed and ruthenium-catalyzed formation of aromatic quinoline intermediates and biomimetic asymmetric reduction.

Enantioselective Synthesis of 2,2,3-Trisubstituted Indolines via Bimetallic Relay Catalysis of α-Diazoketones with Enones

An efficient asymmetric intramolecular trapping of ammonium ylides of α-diazoketones with enones to synthesize indoline derivatives was realized. A Rh(II)/chiral N,N′-dioxide-Sc(III) complex bimetallic relay catalytic system was established. A series of optically active 2,2,3-trisubstituted indolines were obtained in high yields (up to 99%), good enantioselectivities (up to 99% ee), and excellent diastereoselectivities (up to >19:1 dr) under mild reaction conditions.

Synthesis of 2-Substituted Quinolines from 2-Aminostyryl Ketones Using Iodide as a Catalyst

A new protocol for the synthesis of 2-substituted quinolines from 2-aminostyryl ketones has been developed using iodide as a nucleophilic catalyst. Conjugate addition of iodide to 2-aminostyryl ketones yielded the corresponding β-iodoketones, which could have a conformation where the amino and carbonyl groups are proximal through free rotation about the Cα-Cβ single bond. Subsequent condensation between the amino and carbonyl groups followed by elimination of hydrogen iodide provided the corresponding quinolines, with regeneration of the iodide catalyst.

On-Water Synthesis of 2-Substituted Quinolines from 2-Aminochalcones Using Benzylamine as the Nucleophilic Catalyst

On-water synthesis of 2-substituted quinolines from 2-aminochalcone derivatives was developed using benzylamine as the nucleophilic catalyst. Various 2-aminochalcones could be applied to this protocol, and the desired 2-substituted quinoline products were isolated in excellent yields by simple filtration. Furthermore, we elucidated the role of benzylamine in this transformation and provided the detailed reaction mechanism. This protocol has several additional advantages, such as simple operation, broad substrate scope, good functional group tolerance, easy product isolation, recycling of the catalyst, and gram-scale synthesis.

Blue-light-promoted carbon-carbon double bond isomerization and its application in the syntheses of quinolines

A blue-light-promoted carbon-carbon double bond isomerization in the absence of any photoredox catalyst is reported. It provides rapid access to a series of quinolines in good to excellent yields under simple aerobic conditions. The protocol is direct, catalyst-free and operationally convenient.

Organocatalyzed aerobic oxidative Robinson-type annulation of 2-isocyanochalcones: expedient synthesis of phenanthridines

A DBU-catalyzed aerobic oxidative Robinson annulation of 2-isocyanochalcones with active methylene ketones was developed for the expedient synthesis of phenanthridines in high to excellent yields. This unprecedented multistep domino reaction represents a

Catalytic Asymmetric Cascade Using Spiro-Pyrrolidine Organocatalyst: Efficient Construction of Hydrophenanthridine Derivatives

A newly developed SPD (spiro-pyrrolidine) organocatalyst has been demonstrated to enable an asymmetric aza-Michael/Michael/aldol cyclization cascade, in which two six-membered rings (B/C) and three stereocenters have been constructed in a catalytic one-step process. It is so far the most efficient method for construction of hydrophenanthridine derivatives featuring high enantioselectivity. The trans- or cis-fused B/C-rings can be selectively assembled in a substrate-controlled manner. Moreover, this cascade could magnify to gram scale without loss of enanioselectivity.

Cross-Cycloaddition of Two Different Isocyanides: Chemoselective Heterodimerization and [3+2]-Cyclization of 1,4-Diazabutatriene

A new cross-cycloaddition reaction between a wide range of isocyanides and 2-isocyanochalcones (or analogues) was developed for the expeditious synthesis of pyrrolo[3,4-b]indoles under thermal conditions. On the basis of the experimental results and DFT c