19348-61-9

Upstream product

• 578-66-5 8-amino quinoline 
• 85-44-9 phthalic anhydride 

Downstream Products

• 88-96-0 phthalamide 
• 84-66-2 Diethyl phthalate 
• 33757-48-1 N-quinolin-8-yl-benzamide 
• 723259-89-0 2-iodo-N-(quinolin-8-yl)benzamide 
• 1604839-42-0 4-ethyl-3-phenyl-2-(quinolin-8-yl)isoquinolin-1(2H)-one 
• 1604839-33-9 3,4-diphenyl-2-(quinolin-8-yl)isoquinolin-1(2H)-one 

Relevant academic research and scientific papers

Catalytically Relevant Intermediates in the Ni-Catalyzed C(sp2)-H and C(sp3)-H Functionalization of Aminoquinoline Substrates

This Article describes the synthesis and characterization of cyclometalated aminoquinoline NiII σ-aryl and σ-alkyl complexes that have been proposed as key intermediates in Ni-catalyzed C-H functionalization reactions. These NiII complexes serve as competent catalysts for the C-H functionalization of aminoquinoline derivatives with I2. They also react stoichiometrically with I2 to form either aryl iodides or β-lactams within minutes at room temperature. Furthermore, they react with AgI salts at -30 °C to afford isolable five-coordinate NiIII species. The NiIII σ-aryl complexes proved inert toward C(sp2)-I bond-forming reductive elimination under all conditions examined (up to 140 °C in DMF). In contrast, a NiIII σ-alkyl analogue underwent C(sp3)-N bond-forming reductive elimination at 140 °C in DMF to afford a β-lactam product. However, despite the ability of this latter NiIII species to participate in stoichiometric product formation, the complex was not a competent catalyst for β-lactam formation. Overall, these results suggest against the intermediacy of NiIII species in these C-H functionalization reactions.

Erratum: Catalytically Relevant Intermediates in the Ni-Catalyzed C(sp2)-H and C(sp3)-H Functionalization of Aminoquinoline Substrates (J. Am. Chem. Soc. (2019) 141:43 (17382-17387) DOI: 10.1021/jacs.9b09109)

Further analysis of our data revealed that the thermolysis ofNi(III) complex 4b does not lead to C(sp3)-N bondformingreductive elimination to form ?-lactam 3b-H. As such, our claim that this is “the first directly observable example of C(sp3)-N coupling from an isolated NiIII center” is incorrect. Equation 6 should be modified as follows: As a consequence, the statement in the Abstract that “a NiIII s-alkyl analogue underwent C(sp3)-N bond-forming reductive elimination at 140 °C in DMF to afford a ?-lactam product” is also incorrect. The TOC graphic should also be corrected as follows: After the discovery of this major error, we went back and carefully repeated all of the synthesis and reactivity experiments described in the Article to ensure their accuracy and reproducibility. This has led to changes in the yields and in some cases solvent and reaction time for many of the reactions reported therein. The Supporting Information has been updated with revised procedures and spectra as well as updated yields. In addition, we have included in the revised Supporting Information a copy of an updated manuscript with each change highlighted to clearly indicate these revisions. Unlike the error in eq 6, none of these additional changes alters our key conclusions from the original manuscript.FF

Cobalt-Catalyzed Regioselective Carboamidation of Alkynes with Imides Enabled by Cleavage of C-N and C-C Bonds

Through the oxidative addition of cobalt into the N-C(O) bond of phthalimide and the subsequent decarbonylation, we describe an efficient cobalt-catalyzed intermolecular decarbonylative carboamidation of alkynes. High regioselectivities have been achieved for unsymmetrical alkynes (including aryl-alkyl or aryl-aryl) to deliver polysubstituted isoquinolones. To facilitate step economy, a three-component decarbonylative carboamidation of alkynes with phthalic anhydrides and amines has been demonstrated using the current cobalt catalysis.

QUINOLINES THAT MODULATE SERCA AND THEIR USE FOR TREATING DISEASE

Provided herein are quinolines, e.g., a compound of Formula I, pharmaceutical compositions thereof, and methods of their use for treating, preventing, or ameliorating one or more symptoms of a neurological disease, neurodegenerative disorder, or diabetes. Also provided herein are methods of their use for modulating the activity of a sarcoplasmic/endoplasmic reticulum C2+ ATPase.

Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives

The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.

QUINOLINES AND THEIR USE FOR TREATING ENDOPLASMIC RETICULUM STRESS-CAUSED DISEASES

Provided herein are quinolines, e.g., a compound of Formula (I) or (IB), pharmaceutical compositions thereof, and methods of their use for treating, preventing, or ameliorating one or more symptoms of an endoplasmic reticulum stress-caused disease. Also provided herein are methods of their use for reducing endoplasmic reticulum stress and modulating the activity of a sarcoplasmic/endoplasmic reticulum Ca2+ ATPase.

Cobalt-Catalyzed Carbonylation of C(sp2)-H Bonds with Azodicarboxylate as the Carbonyl Source

A novel and efficient approach for the C(sp2)-H bond carbonylation of benzamides has been developed using stable and inexpensive Co(OAc)2·4H2O as the catalyst and the commercially available and easily handling azodicarboxylates as the nontoxic carbonyl source. A broad range of substrates bearing diverse functional groups were tolerated. This is the first example where cobalt-catalyzed C(sp2)-H bond carbonylation occurs with azodicarboxylate as the carbonyl source.

The coordination chemistry of fluorescent pyridinyl- and quinolinyl-phthalimide ligands with the {AuI-PPh3} cationic unit

The new mono-dentate ligands, 2-(2-aminoethyl)-N-phthalimido-pyridine (L4) and 8-amino-N-phthalimido-quinoline (L6), were synthesised using a solvent-free melt method. These ligands together with L 1-3,5 (3-amino-N-phthalimido-pyridine; 3-aminomethyl-N-phthalimido- pyridine; 4-aminomethyl-N-phthalimido-pyridine; 3-amino-N-phthalimido-quinoline) were then used to access six luminescent AuI complexes of the generic type {Ph3P-Au-Ln}(OTf). X-Ray crystallography has been used to structurally characterise three of the complexes showing that in the cases of L1 and L3 the complexes adopt an approximately linear P-Au-N coordination geometry. However, in the case of the sterically demanding L6 the structure shows distortions within the ligand and deviations from a linear coordination geometry. Solution state 1H and 31P{1H} NMR confirmed that the proposed formulations and coordination modes exist in solution. At room temperature the photophysical studies showed that the emission from each of the six complexes was in the visible region (395-475 nm) and assigned to a ligand-centred fluorescence (τ 10 ns) in each case. The Royal Society of Chemistry 2009.

Fragmentation of isomeric N-quinolinylphthalimides on electron impact ionization

The isomeric 2-, 3-, 5-, 6- and 8-quinolinylphthalimides give rise to different electron impact ionization mass spectra, which permit easy distinction. The specific fragmentation processes are rationalized in terms of proximity effects and stabilization of cyclic ion structures. Collision-induced dissociation spectra were used to support the proposed ion structures of major fragment ions.