36107-01-4

Upstream product

• 578-66-5 8-amino quinoline 
• 6942-98-9 5-chloro-8-nitroquinoline 
• 34522-74-2 5,7-dichloro-8-nitro-quinoline 
• 64-19-7 acetic acid 
• 148-24-3 8-quinolinol 
• 60-29-7 diethyl ether 
• 773-76-2 chloroxine 

Relevant academic research and scientific papers

Structural Diversity in a New Series of Halogenated Quinolyl Salicylaldimides-Based FeIII Complexes Showing Solid-State Halogen-Bonding/Halogen···Halogen Interactions

A new series of tridentate N-8-quinolyl-salicylaldimine ligands, Hqsal-5,7-X2 [X = Cl(1), Br(2), I(3)], halo-substituted at the 5,7 position of the aminoquinoline moiety and their corresponding complexes with FeIII were synthesized and formulated as [Fe(qsal-5,7-X2)(NCS)(MeO)]2·solv. (X = Cl (1a), Br (2a), I (3a, solv = 1/2MeOH), [Fe4(qsal-5,7-X2)4(NCS)2(MeO)2]·solv. (X = Br (2b), I (3b; solv = 4CH2Cl2)) by single-crystal X-ray diffraction analysis. 1a and 2a are isostructural dimers where each FeIII metal ion, showing a distorted octahedral environment, is bound by a N,N,O tridentate (qsal-5,7-X2)- (X = Cl and Br) ligand, a N-coordinated SCN- anion, and a bridging methanolate anion. 2b and 3b are centrosymmetric tetramers where each FeIII is bound by three nitrogen atoms and three oxygen atoms derived from a tridentate (qsal-5,7-X2)- (X = Br and I), a SCN-, a bridging methanolate anion, and a bridging μ2-oxy moiety. In 3b, the iodine atoms dominate the packing interactions through the establishment of a halogen-bonding network. The magnetic behavior of 1a-3a dimers and 2b-3b tetramers indicate the presence of strong antiferromagnetic interactions between FeIII centers (S = 5/2), mediated by the alkoxy bridges. Experimental data can be modeled with an isotropic Hamiltonian, H = -2J(S1 · S2) for dimers (J = -15 cm-1) and H = -2J(S2 · S3) - 2J′(S1 · S2 + S3 · S4), for tetramers (J = -24 cm-1, J′ = -11 cm-1). The magnetic behavior of 1a-3a dimers indicates the presence of strong antiferromagnetic interactions between FeIII centers (S = 5/2), mediated by the alkoxy bridges. 2b and 3b show the same magnetic behavior since they contains analogous bridges between paramagnetic centers, but for a linear tetramer. Density functional theory (DFT) calculations, based on hybrid functional mPW1PW paralleled by the Def2SVP all-electron split-valence basis sets, support the experimental results, showing that monomers could possibly show a spin crossover (SCO) behavior, even though the formation of complexes with an even number of metal ions results in the strong antiferromagnetic interactions. Accordingly, broken symmetry DFT calculations carried out on 1a clearly show that the antiferromagnetic coupling of the two HS FeIII centers results in the lowest energy electron configuration of the complex.

Palladium-Catalyzed Electrochemical C-H Bromination Using NH4Br as the Brominating Reagent

The palladium-catalyzed electrochemical C-H bromination of benzamide derivatives under divided cells is developed, in which NH4Br serves as a brominating reagent and electrolyte. The protocol avoids the use of chemical oxidants and provides an alternative method for the synthesis of aryl bromides.

Remote radical halogenation of aminoquinolines with aqueous hydrogen halide (HX) and oxone

Simple and halide-atom economical HX reagents (X = Cl, Br and I) were applied to the remote C–H bond halogenation reaction of 8-aminoquinoline amides. This strategy features a broad substrate scope and good functional group tolerance. A series of C5-halog

A general method for the metal-free, regioselective, remote C-H halogenation of 8-substituted quinolines

An operationally simple and metal-free protocol for geometrically inaccessible C5-H halogenation of a range of 8-substituted quinoline derivatives has been established. The reaction proceeds under air, with inexpensive and atom economical trihaloisocyanuric acid as a halogen source (only 0.36 equiv.), at room temperature. Exceptionally high generality with respect to quinoline is observed, and in most instances, the reaction proceeded with complete regioselectivity. Quinoline with a variety of substituents at the 8-position gave, exclusively, the C5-halogenated product in good to excellent yields. Phosphoramidates, tertiary amides, N-alkyl/N,N-dialkyl, and urea derivatives of quinolin-8-amine as well as alkoxy quinolines were halogenated at the C5-position via remote functionalization for the first time. This methodology provides a highly economical route to halogenated quinolines with excellent functional group tolerance, thus providing a good complement to existing remote functionalization methods of quinolin-8-amide derivatives and broadening the field of remote functionalization. The utility of the method is further showcased through the synthesis of several compounds of biological and pharmaceutical interest.

Palladium-Catalyzed ortho-Selective C-H Chlorination of Benzamide Derivatives under Anodic Oxidation Conditions

The palladium-catalyzed ortho-selective chlorination of N-quinolinylbenzamide derivatives with hydrochloric acid was achieved under anodic oxidation conditions. The use of 5,7-dichloro-8-quinolinyl group as directing group was effective for the selective

Preparation of aniline derivatives

In the present invention, provided is a novel manufacturing method of aniline derivative, which is more simple and eco-friendly and takes less cost compared with an existing synthesizing aniline method, comprising a step of manufacturing chemical formula 1 by making chemical formula 2 react with chemical formula 3 under catalyst, bases and solvents wherein the manufacturing method aniline derivative is manufactured through one pot in a simple manner and accordingly easily removes the solvent with use of distillation under reduced pressure after reaction.

One-pot conversion of phenols to anilines via Smiles rearrangement

A convenient one-pot synthesis of phenols to anilines using 2-chloroacetamide/K2CO3/DMF system catalyzed by KI via Smiles rearrangement has been described. The synthesis of extensive amino aromatic products from phenols containing electron withdrawing group, has been performed in moderate to excellent yields to demonstrate the potentiality of this method in bio-medicinal and pharmaceutical applications.

Substituted 8-sulfonamidoquinolines

Certain sulfonamidoquinolines and metal complexes thereof both of which are soluble in essentially water-immiscible organic solvents. The sulfonamidoquinolines have the structural formula STR1 where the R, R1 and R2 groups and m and n are as defined in the specification and claims hereof. Solutions of the sulfonamidoquinolines and the metal complexes thereof in essentially water-immiscible organic solvents.