181867-44-7

Upstream product

• 99-90-1 para-bromoacetophenone 
• 552-89-6 2-nitro-benzaldehyde 
• 1777-57-7 p-bromobenzoylmethylenetriphenylphosphorane 

Downstream Products

• 1256639-93-6 C₁₈H₁₄BrN₃O₃S 
• 24641-31-4 2-(4-bromophenyl)quinoline 
• 89671-78-3 (4-bromophenyl)(1H-indol-2-yl)methanone 
• 19062-78-3 2-(4-bromophenyl)quinoline 1-oxide 
• 1312162-99-4 (R)-2-(4-bromophenyl)-1,2,3,4-tetrahydroquinoline 
• 1016275-42-5 (S)-2-(4-bromophenyl)-1,2,3,4-tetrahydroquinoline 
• 1432624-48-0 (E)-3-(2-aminophenyl)-1-(4-bromophenyl)prop-2-en-1-one 
• 1455213-48-5 (2’R,3’S,4’S)-1-acetyl-2’-benzoyl-4’-(2-oxo-1-(4-bromophenylethyl))-2-oxo-1’-tosylspiro[indoline-3,3’-tetrahydroquinoline] 

Relevant academic research and scientific papers

Visible-light-driven Cadogan reaction

Visible-light-driven photochemical Cadogan-type cyclization has been discovered. The organic D-A type photosensitizer 4CzIPN found to be an efficient mediator to transfer energy from photons to the transient intermediate that breaks the barriers of deoxygenation in Cadogan reaction and enables a mild metal-free access to carbazoles and related heterocycles. DFT calculation results indicate mildly endergonic formation of the intermediate complex of nitrobiarenes and PPh3, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.

Synthesis of 1,4-dihydropyrazolo[4,3-b]indoles via intramolecular C(sp2)-N bond formation involving nitrene insertion, DFT study and their anticancer assessment

We herein report a new synthetic route for a series of unreported 1,4-dihydropyrazolo[4,3-b]indoles (6–8) via deoxygenation of o-nitrophenyl-substituted N-aryl pyrazoles and subsequent intramolecular (sp2)-N bond formation under microwave irradiation expedite modified Cadogan condition. This method allows access to NH-free as well as N-substituted fused indoles. DFT study and controlled experiments highlighted the role of nitrene insertion as one of the plausible reaction mechanisms. Furthermore, the target compounds exhibited cytotoxicity at low micromolar concentration against lung (A549), colon (HCT-116), and breast (MDA-MB-231, and MCF-7) cancer cell lines, induced the ROS generation and altered the mitochondrial membrane potential of highly aggressive MDA-MB-231 cells. Further investigations revealed that these compounds were selective Topo I (6h) or Topo II (7a, 7b) inhibitors.

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

Visible-Light Induction/Br?nsted Acid Catalysis in Relay for the Enantioselective Synthesis of Tetrahydroquinolines

An efficient method merging Br?nsted acid catalysis with visible-light induction for the highly enantioselective synthesis of tetrahydroquinolines has been developed. This mild process directly transforms 2-aminoenones into 2-substituted tetrahydroquinolines with excellent enantioselectivities through a relay visible-light-induced cyclization/chiral phosphoric acid-catalyzed transfer hydrogenation reaction.

Asymmetric synthesis of CF3-containing tetrahydroquinoline: Via a thiourea-catalyzed cascade reaction

An organocatalytic asymmetric method for the synthesis of 2-CF3 tetrahydroquinoline has been achieved. The cascade reaction of 2-aminochalcones with β-CF3 nitroalkenes afforded the products bearing three contiguous stereogenic centers in good yields with excellent diastereoselectivities and enantioselectivities.

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

Cinchona-based squaramide-catalysed cascade aza-Michael-Michael addition: Enantioselective construction of functionalized spirooxindole tetrahydroquinolines

An efficient enantioselective cascade aza-Michael-Michael addition reaction catalysed by a chiral bifunctional tertiary amine-squaramide catalyst has been developed. This cascade reaction proceeded well under mild conditions, furnishing highly functionalized spirooxindole tetrahydroquinolines with three contiguous stereocenters in excellent yields with excellent diastereoselectivities (>25:1 dr) and high enantioselectivities (up to 94% ee). The Royal Society of Chemistry 2013.

Selective reduction of nitroarenes by a Hantzsch 1,4-dihydropyridine: A facile and efficient approach to substituted quinolines

An efficient reductive cyclization of o-nitrocinnamoyl compounds was achieved by employing a Hantzsch 1,4-dihydropyridine ester as a biomimetic reducing agent in the presence of catalytic palladium on carbon. This approach was successfully applied to the synthesis of substituted quinolines. Georg Thieme Verlag Stuttgart ? New York.

Synthesis and biological activity of 4,6-substituted aryl-1-acetyl pyrimidine-2-ols

The synthesis of 4-(4'-bromophenyl)-6-substituted aryl-1-acetyl-pyrimidine-2-ols have been reported. The synthesized derivatives were characterized by elemental analysis and spectral data (IR and 1H NMR). All the synthesized derivatives have been evaluated for their antimicrobial and anthelmintic activities against microbes and helminthes.