1128-62-7

Upstream product

• 877-42-9 6-Bromo-2-methyl-quinoline 
• 109-92-2 ethyl vinyl ether 
• 540-37-4 p-aminoiodobenzene 
• 5326-47-6 2-amino-5-iodobenzoic acid 
• 53279-83-7 (2-amino-5-iodophenyl)methanol 
• 123-42-2 4-Hydroxy-4-methyl-2-pentanone 
• 99471-71-3 2-amino-5-iodobenzaldehyde 
• 123-73-9 crotonaldehyde 
• 123-63-7 paracetaldehyde 

Downstream Products

• 1372118-47-2 6-((4-methoxyphenyl)ethynyl)quinoline-2-carbaldehyde 
• 108166-03-6 2-methylquinoline-6-carbaldehyde 
• 1608092-52-9 C₂₅H₂₁IN₂ 
• 156138-94-2 2-methyl-5-nitro-6-phenylaminoquinoline 

Relevant academic research and scientific papers

Cooperative Lewis Acid Catalysis for the Enantioselective C(sp3)-H Bond Functionalizations of 2-Alkyl Azaarenes

Herein, we describe the enantioselective C(sp3)-H bond functionalizations of 2-alkyl azaarenes using a cooperative dual Lewis acid catalysis. An achiral Lewis acid activates the unactivated azaarene partner without the need for a strong base. Orthogonally, a chiral-at-metal Lewis acid catalyst enables LUMO lowering and induces chirality. This method tolerates a range of complex molecular scaffolds and exhibits good to excellent yields and selectivity while accepting a wide variety of functional groups.

A two-photon fluorescent probe for viscosity imaging in vivo

A new two-photon fluorescent probe (MCN) for viscosity imaging was developed based on a 6-substituted quinoline framework. MCN showed an excellent “off-on” fluorescence response (ca. 90-fold enhancement) with viscosity increasing in the glycerol-water viscosity system. MCN showed great sensitivity to viscosity (R2 = 0.98, x = 0.65), which gave rise to cell imaging for micro-viscosity or real-time cell imaging during apoptosis with low cytotoxicity under two-photon excitation (λex = 800 nm). Fluorescence lifetime imaging (FLIM) of living HeLa cells stained with MCN revealed that the intracellular average viscosity value was 73.45 ± 21.55 cP in cytosol. Imaging in living tissue slices indicated that MCN can work in deep tissue (～130 μM) under two-photon excitation. Moreover, MCN also showed the capacity for in vivo imaging viscosity in zebrafish with obvious fluorescence emission.

Synthesis of quinolines and naphthyridines: Via catalytic retro-aldol reaction of β-hydroxyketones with ortho -aminobenzaldehydes or nicotinaldehydes

A Cu(i)-catalyzed retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes and nicotinaldehydes is reported that produces a range of quinolines and naphthyridines with high efficiency and selectivity. This reaction uses β-hydroxyketones as a regiospecific ketone-protected enolate source via copper-catalyzed retro-aldol Cα-Cβ bond cleavage. The in situ generated copper enolate undergoes kinetically favorable cyclization with ortho-amino aryl aldehydes to produce quinolines and naphthyridines in a chemo- and regioselective manner. The mild and weakly basic reaction conditions also suppress possible side reactions of benzaldehydes under strongly basic conditions, resulting in improved reaction yields.

Rapid and efficient copper-catalyzed finkelstein reaction of (hetero)aromatics under continuous-flow conditions

A general, rapid, and efficient method for the copper-catalyzed Finkelstein reaction of (hetero)aromatics has been developed using continuous flow to generate a variety of aryl iodides. The described method can tolerate a broad spectrum of functional groups, including N-H and O-H groups. Additionally, in lieu of isolation, the aryl iodide solutions were used in two distinct multistep continuous-flow processes (amidation and Mg-I exchange/nucleophilic addition) to demonstrate the flexibility of this method.

Storable arylpalladium(II) reagents for alkene labeling in aqueous media

We show that arylpalladium(II) reagents linked to biotin and indocyanine dye residues can be prepared by decarboxylative palladation of appropriately substituted electron-rich benzoic acid derivatives. When prepared under the conditions described, these organometallic intermediates are tolerant of air and water, can be stored for several months in solution in dimethyl sulfoxide, and permit biotin- and indocyanine dye-labeling of functionally complex olefinic substrates in water by Heck-type coupling reactions.

Synthesis of novel quinaldine-based squaraine dyes: Effect of substituents and role of electronic factors

(Chemical Equation Presented) Condensation of squaric acid with quinaldinium salts containing electron-donating substituents gave only the semisquaraines. However, with salts possessing electronegative and electron-withdrawing groups, the squaraine dyes were isolated in quantitative yields. The semisquaraines formed undergo condensation with highly nucleophilic salts yielding the unsymmetrical squaraine dyes. These results demonstrate the role of electronic factors and provide valuable information for the design of efficient squaraine-based sensitizers that can have potential applications in photodynamic therapy.