1204482-06-3

Upstream product

• 536-38-9 4-chlorobenzoylmethyl bromide 
• 1777-56-6 4-chlorobenzoylmethylenetriphenylphosphorane 
• 24668-08-4 1-(4-chlorophenyl)-3-(2-nitrophenyl)prop-2-en-1-one 
• 552-89-6 2-nitro-benzaldehyde 
• 99-91-2 para-chloroacetophenone 
• 24668-08-4 (E)-1-(4-chlorophenyl)-3-(2-nitrophenyl)-2-propen-1-one 

Downstream Products

• 1266349-63-6 1-(4-chlorophenyl)-2-((2S,3S,4R)-3-nitro-2-phenyl-1,2,3,4-tetrahydroquinolin-4-yl)ethanone 
• 1266349-64-7 1-(4-chlorophenyl)-2-((2S,3S,4R)-3-nitro-2-m-tolyl-1,2,3,4-tetrahydroquinolin-4-yl)ethanone 
• 1266349-65-8 1-(4-chlorophenyl)-2-((2S,3S,4R)-2-(2-chlorophenyl)-3-nitro-1,2,3,4-tetrahydroquinolin-4-yl)ethanone 
• 1266349-40-9 (E)-3-(2-((E)-2-chlorobenzylideneamino)phenyl)-1-(4-chlorophenyl)prop-2-en-1-one 
• 1266349-38-5 (E)-3-(2-((E)-benzylideneamino)phenyl)-1-(4-chlorophenyl)prop-2-en-1-one 
• 1266349-39-6 (E)-1-(4-chlorophenyl)-3-(2-((E)-3-methylbenzylideneamino)phenyl)prop-2-en-1-one 
• 1312163-01-1 (+)-(R)-2-(4-chlorophenyl)-1,2,3,4-tetrahydroquinoline 

Relevant academic research and scientific papers

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.

Tandem Cyclization?Annulation of α-Acidic Isocyanides with 2-Methyleneaminochalcones: Synthesis of Pyrrolo[2,3-c]quinoline Derivatives

Tandem cyclization-annulation of tosylmethyl isocyanide and isocyanoacetate with 2-methyleneaminochalcones as aza-1,5-dielectrophiles has been successfully developed. These domino transformations feature simultaneous formation of three bonds and two rings

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.

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.

Acrylamide in Rauhut-Currier reaction; intramolecular isomerization of activated alkenes for quinolone synthesis

Acrylamides are fundamental Michael acceptors which have been used profoundly in synthetic, medicinal and polymer chemistry. However, due to their lower reactivity they have been least used in Morita-Baylis-Hillman (MBH) reaction and have been out of its vinylogus version Rauhut Currier (RC) reaction. Herein, use of acrylamide in RC reaction is being presented. Intramolecular RC reaction followed by [1,3]-H shift led to the synthesis of quinolone moiety. DABCO catalyzed IRC reaction of acrylamide at 80 °C in presence of water, was found to work on a number of precursors. En route chemo selective, gram scale method for ambiphilic, versatile precursor 2-amino chalcone is also reported. Chemoselective and economical conversion of 2-nitro chalcone to 2-aryl quinoline has also been developed.

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.

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

One pot synthesis of pyrrolo[3,4-c]quinolinone/pyrrolo[3,4-c]quinoline derivatives from 2-aminoarylacrylates/2-aminochalcones and tosylmethyl isocyanide (TosMIC)

An efficient and practical synthetic approach to access to 2H-pyrrolo[3,4-c]quinolin-4(5H)-one/2H-pyrrolo[3,4-c]quinoline derivatives by the reaction of 2-aminoarylacrylates/2-aminochalcones and tosylmethyl isocyanide (TosMIC) via a one pot van Leusen rea