1532-84-9

Usage

InChI:InChI=1/C9H8N2/c10-9-8-4-2-1-3-7(8)5-6-11-9/h1-6H,(H2,10,11)

Upstream product

• 119-65-3 isoquinoline 
• 19658-76-5 1-nitro-isoquinoline 
• 76195-91-0 1-<(α-hydroxy-3,4-dimethoxybenzylidene)amino>isoquinoline 
• 108-88-3 toluene 
• 1532-72-5 isoquinoline N-oxide 
• 7159-36-6 4-isoquinolinecarboxylic acid 
• 850705-46-3 C₁₅H₁₆N₂O₄ 
• 19493-44-8 1-chloroisoquinoline 
• 1532-71-4 1-bromoisoquinoline 
• 1198-30-7 1-isoquinolinecarbonitrile 
• 593-56-6 N-methoxylamine hydrochloride 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 6092-80-4 phenoxyamine hydrochloride 
• 1721-93-3 1-methylisoquinoline 

Downstream Products

• 116915-71-0 [1]isoquinolyl-picryl-amine 
• 51640-00-7 N-(isoquinolin-1-yl)acetamide 
• 70845-68-0 2-Phenyl-imidazo<2,1-a>isochinolin 
• 859962-83-7 (2,4-dinitro-phenyl)-[1]isoquinolyl-amine 
• 75704-51-7 5,6,7,8-tetrahydroisoquinoline-1-amine 
• 491-30-5 1-hydroxyisoquinoline 
• 19493-44-8 1-chloroisoquinoline 
• 125344-95-8 (1R,2S,6R,7R)-10-Benzhydrylidene-4-isoquinolin-1-yl-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 
• 4508-50-3 Z-1-(2-cyanophenyl)-2-cyanoethene 
• 18454-47-2 E-1-(2-cyanophenyl)-2-cyanoethene 
• 69707-18-2 Imidazo[2,1-a]isoquinoline-2-carboxylic acid ethyl ester 
• 86938-79-6 2-(3,4-Dimethoxyphenyl)imidazo<2,1-a>isoquinoline 
• 61001-11-4 2-(3-chlorophenyl)imidazo[2,1-a]isoquinoline 
• 3174-61-6 C₁₅H₁₂N₄ 

Relevant academic research and scientific papers

Method for synthesizing 1-aminoisoquinoline skeleton by rhodium-catalyzed 4-phenyl oxadiazolone and vinylene carbonate

The invention discloses a method for generating 1-aminoisoquinoline and a derivative thereof through a rhodium-catalyzed reaction of a 4-phenyl oxadiazolone compound and vinylene carbonate. According to the invention, a 4-phenyl oxadiazolone compound is used as a raw material and reacts with vinylene carbonate under the catalysis of transition metal rhodium to generate an isoquinoline ring. The synthesis operation steps are simple, the atom economy is high, the application range of the substrate is wide, the post-treatment operation is simpler, the implementation feasibility is high, and a foundation is laid for industrial production and wide application of the aminoisoquinoline compound.

Catalyst-free synthesis of substituted pyridin-2-yl, quinolin-2-yl, and isoquinolin-1-yl carbamates from the corresponding hetaryl ureas and alcohols

A novel catalyst-free synthesis ofN-pyridin-2-yl,N-quinolin-2-yl, andN-isoquinolin-1-yl carbamates utilizes easily accessibleN-hetaryl ureas and alcohols. The proposed environmentally friendly technique is suitable for the good-to-high yielding synthesis of a wide range ofN-pyridin-2-yl orN-quinolin-2-yl substituted carbamates featuring electron-donating and electron-withdrawing groups in the azine rings and containing various primary, secondary, and even tertiary alkyl substituents at the oxygen atom (48-94%; 31 examples). The DFT calculation and experimental study showed that the reaction proceeds through the intermediate formation of hetaryl isocyanates. The method can be applied to obtainN-isoquinolin-1-yl carbamates, although in lower yields, and ethyl benzo[h]quinolin-2-yl carbamate has also been successfully synthesized (68%).

Heteroarylation method of amine

The invention discloses a heteroarylation method of amine, and the method comprises the following steps of: mixing an amine compound, heteroaromatic hydrocarbon, a photocatalyst and an organic solventto obtain a solution A; and in an inert gas atmosphere, irradiating the solution A with visible light, and carrying out reaction to obtain a heteroarylated product of amine. According to the method,under mild conditions, free radical coupling of amine compounds and heteroaromatic compounds is efficiently achieved through visible light irradiation, and various heteroarylamines are synthesized. The method has good functional group compatibility and high regioselectivity, can be further applied to later modification of bioactive molecules, and shows a good industrial application prospect.

Rhodium(III)-Catalyzed Oxidative Annulation of Amidines with Alkynes via Sequential C?H Bond Activation

In this paper, a rhodium-catalyzed sequential two-fold ortho-C?H functionalization of N-phenylbenzimidamide with internal alkyne is reported. The double C?H activations proved viable in a one-pot fashion with the assistance of C=N and C?N bonds, providing a series of benzimidazoisoquinolines with high levels of positional selectivity control. The operationally simple transformation showed high functional group compatibility and featured the cleavage of C?H bonds located on different a moiety of the N-phenylbenzimidamide substrates. Detailed mechanistic studies provided strong support for C?H bond cleavage on the N-phenyl ring to be preferential compared with C?H bond cleavage on C-phenyl ring. As a multifunctional catalytic platform, the rhodium catalyst conducted two independent and compatible catalytic cycles in one pot.

Metal-free, redox-neutral, site-selective access to heteroarylamine via direct radical?radical cross-coupling powered by visible light photocatalysis

Transition-metal-catalyzed C?N bond-forming reactions have emerged as fundamental and powerful tools to construct arylamines, a common structure found in drug agents, natural products, and fine chemicals. Reported herein is an alternative access to heteroarylamine via radical?radical cross-coupling pathway, powered by visible light catalysis without any aid of external oxidant and reductant. Only by visible light irradiation of a photocatalyst, such as a metal-free photocatalyst, does the cascade single-electron transfer event for amines and heteroaryl nitriles occur, demonstrated by steady-state and transient spectroscopic studies, resulting in an amine radical cation and aryl radical anion in situ for C?N bond formation. The metal-free and redox economic nature, high efficiency, and site-selectivity of C?N cross-coupling of a range of available amines, hydroxylamines, and hydrazines with heteroaryl nitriles make this protocol promising in both academic and industrial settings.

Direct Hydroxylation and Amination of Arenes via Deprotonative Cupration

Deprotonative directed ortho cupration of aromatic/heteroaromatic C-H bond and subsequent oxidation with t-BuOOH furnished functionalized phenols in high yields with high regio- and chemoselectivity. DFT calculations revealed that this hydroxylation reaction proceeds via a copper (I → III → I) redox mechanism. Application of this reaction to aromatic C-H amination using BnONH2 efficiently afforded the corresponding primary anilines. These reactions show broad scope and good functional group compatibility. Catalytic versions of these transformations are also demonstrated.

Ligandless copper-catalyzed coupling of heteroaryl bromides with gaseous ammonia

A range of different N- and S-containing heterocyclic bromides can be efficiently coupled with gaseous ammonia in the presence of copper(II) acetylacetonate [Cu(acac)2] as catalyst and in the absence of additional ligands. Unstable aminothiophenes and aminobenzothiophenes can be further reacted in situ to afford functionalized derivatives. Copyright

Mild and highly selective palladium-catalyzed monoarylation of ammonia enabled by the use of bulky biarylphosphine ligands and palladacycle precatalysts

A method for the Pd-catalyzed arylation of ammonia with a wide range of aryl and heteroaryl halides, including challenging five-membered heterocyclic substrates, is described. Excellent selectivity for monoarylation of ammonia to primary arylamines was achieved under mild conditions or at rt by the use of bulky biarylphosphine ligands (L6, L7, and L4) as well as their corresponding aminobiphenyl palladacycle precatalysts (3a, 3b, and 3c). As this process requires neither the use of a glovebox nor high pressures of ammonia, it should be widely applicable.

NOVEL CATALYSTS

The present invention provides novel compounds and ligands that are useful in transition metal catalyzed cross-coupling reactions. For example, the compounds and ligands of the present invention are useful in palladium or gold catalyzed cross-coupling reactions.

A highly versatile catalyst system for the cross-coupling of aryl chlorides and Amines

The syntheses of 2-(di-tertbutylphosphino)-N,N-dimethylaniline (L1, 71%) and 2-(di-1-adamantylphosphino)-N,N-dimethylaniline (L2, 74%), and their application in BuchwaldHartwig amination, are reported. In combination with [Pd(allyl)Cl]2 or [Pd(cinnamyl)Cl]2, these structurally simple and air-stable P,N ligands enable the cross-coupling of aryl and heteroaryl chlorides, including those bearing as substituents enolizable ketones, ethers, esters, carboxylic acids, phenols, alcohols, olefins, amides, and halogens, to a diverse range of amine and related substrates that includes primary alkyl- and arylamines, cyclic and acyclic secondary amines, N-H imines, hydrazones, lithium amide, and ammonia. In many cases, the reactions can be performed at low catalyst loadings (0.5-0.02 mol % Pd) with excellent functional group tolerance and chemoselectivity. Examples of cross-coupling reactions involving 1,4-bromochlorobenzene and iodobenzene are also reported. Under similar conditions, inferior catalytic performance was achieved when using Pd(OAc)2, PdCl2, [PdCl2(cod)] (cod = 1,5-cyclooctadiene), [PdCl 2(MeCN)2], or [Pd2(dba)3] (dba = dibenzylideneacetone) in combination with L1 or L2, or by use of [Pd(allyl)Cl]2 or [Pd(cinnamyl)Cl]2 with variants of L1 and L2 bearing less basic or less sterically demanding substituents on phosphorus or lacking an ortto-dimethylamino fragment. Given current limitations associated with established ligand classes with regard to maintaining high activity across the diverse possible range of C-N coupling applications, L1 and L2 represent unusually versatile ligand systems for the cross-coupling of aryl chlorides and amines