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Biologically active compositions of matter comprising substituted isoquinolines and salts thereof. Certain of the compounds and their salts are novel. Acaricidal, fungicidal, herbicidal and insecticidal activity is demonstrated. In particular 3-chloro-5-acetamido-isoquinoline shows good activity as a selective pre-emergence herbicide, and 4-bromo-5-nitro-isoquinoline shows good fungicidal activity against Erysiphe graminis (wheat powdery mildew).

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Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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A method for producing a biaryl compound, comprising reacting an aromatic organic compound with at least one compound selected from the group consisting of aromatic organoboron compounds and boroxine compounds, in the presence of a zero-valent nickel catalyst, phosphine ligand and base.

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Isoquinoline – Wikipedia,
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While numerous organo(metallic)catalyst systems were documented for dearomative hydroboration of N-aromatics, alkoxide base catalysts have not been disclosed thus far. Described herein is the first example of alkoxide-catalyzed hydroboration of N-heteroaromatics including pyridines, providing a broad range of reduced N-heterocycles with high efficiency and selectivity. Mechanistic studies revealed an unprecedented counterintuitive dearomatization pathway, in which 1) pyridine-BH3 adducts undergo a hydride attack by alkoxyborohydrides, 2) in situ generated BH3 serves as a catalytic promoter, and 3) 1,4-dihydropyridyl borohydride is in a predominant resting state.

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Isoquinoline – Wikipedia,
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The invention discloses a synthesis method of an acylated quinoline or isoquinoline derivative, belongs to the field of organic synthesis, and aims to solve the problems of complicated reaction, severe conditions and low environmental friendliness in the conventional acylated quinoline or isoquinoline derivative synthesis method. The synthesis method comprises the following steps: under a nitrogenatmosphere, adding quinoline or isoquinoline and benzoyl formic acid which are used as reaction raw materials, persulfate used as an oxidant and a metal iridium compound used as a visible light catalyst into a reaction container together with an organic solvent for reaction under a visible light illumination condition, and at the end of the reaction, filtering, concentrating, separating and purifying a reaction system, thus obtaining the acylated quinoline or isoquinoline derivative. According to the synthesis method, under the nitrogen atmosphere, the reaction system is placed under a visible light source for illumination to realize reaction, so that the whole reaction process is safe and environmentally friendly, reaction conditions are simple, and operation steps are convenient; the synthesis method belongs to an environment-friendly chemical process.

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Reference:
Isoquinoline – Wikipedia,
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Metal?Lewis acid cooperation provides new opportunities in catalysis. In this work, we report a new type of palladium?borane cooperation involving anionic Pd0 species. The air-stable DPB palladium complex 1 (DPB=diphosphine-borane) was prepared and reacted with KH to give the Pd0 borohydride 2, the first monomeric anionic Pd0 species to be structurally characterized. The boron moiety acts as an acceptor towards Pd in 1 via Pd?B interaction, but as a donor in 2 thanks to B-H-Pd bridging. This enables the activation of C?Cl bonds and the system is amenable to catalysis, as demonstrated by the hydro-/deutero-dehalogenation of a variety of (hetero)aryl chlorides (20 examples, average yield 85 %).

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Isoquinoline – Wikipedia,
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The synthesis and the 125I-apamin binding studies of original C-5- and C-8-substituted 1-(3,4-dimethoxy-benzyl)-2,2-dimethyl-1,2,3,4- tetrahydroisoquinoliniums and 1-(3,4-dimethoxy-benzyl)-6,6-dimethyl-4,5,6,7- tetrahydrothieno[2,3-c]pyridiniums were performed in order to find a reversible and selective SK channel blocker structurally related to N-methyl-laudanosine and N-methyl-noscapine. A bulky alkyl substituent in the C-8 position of the tetrahydroisoquinoline produces a clear increase in the affinity for the apamin sensitive binding sites. The presence of an electron-withdrawing group in the C-5 and C-8 positions is not a suitable substitution for the affinity of drugs structurally related to N-methyl-laudanosine. Thiophenic analogues and 8-methoxy derivatives possess a poor affinity for the apamin sensitive binding sites. Electrophysiological studies performed with the most effective compound showed a blockade of the apamin sensitive afterhyperpolarization in rat dopaminergic neurons.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H1544N – PubChem

 

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A visible-light-induced C?H cyanoalkylation of heteroarenes was described, in which cycloketone oximes were readily transformed into carbon-centered radicals with a terminal cyano-group via N?O/C?C bonds cleavage in one phtochemical step. This reaction protocol displayed a broad substrate scope of heterocycle compounds, and it provided a promising strategy for the installation of cyanoalkyl groups onto heteroarenes.

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NHC-Catalyzed 1,2-Selective Hydroboration of Quinolines

Selective dearomative transformation of readily available N-heteroarenes is a powerful tool accessing useful synthetic building units. Described herein is the NHC-catalyzed 1,2-selective hydroboration of quinolines with high functional group tolerance. Dihydroquinoline products could be isolated as their amide derivatives upon in situ N-protection, thus offering high synthetic utility of the current procedure. Combined experimental and computational studies revealed that the observed regioselectivity can be rationalized by proposing a six-membered transition state that collectively incorporates NHC catalyst, hydroborane reductant, and protonated quinoline substrate.

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Isoquinoline – Wikipedia,
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N-heterocyclic carbene catalyzed enantioselective [3 + 2] dearomatizing annulation of saturated carboxylic esters with n-iminoisoquinolinium ylides

The dearomatizing annulation reaction is a significant challenge in organic chemistry. The direct activation of alpha-carbons of simple saturated esters, as nucleophiles, is an important synthesis strategy. In the present study, we disclose [3 + 2] dearomatizing annulation reactions with direct activating alpha-carbons of saturated carboxylic esters and N-iminoisoquinolinium ylides, which possess highly enantioselective characteristics, catalyzed by N-heterocyclic carbenes (NHCs). The protocol achieves isoquinoline dearomatization and the construction of tricyclic chiral products under mild conditions with good yield, substrate tolerance, and diastereoselectivity as well as excellent enantioselectivity.

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Isoquinoline – Wikipedia,
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Regioexhaustive Functionalization of the Carbocyclic Core of Isoquinoline: Concise Synthesis of Oxoaporphine Core and Ellipticine

A general and versatile strategy has been developed for the functionalization of the carbocyclic core of the isoquinoline. This regioexhaustive approach employs electrophilic halogenation as a toolbox methodology and delivers highly decorated intermediates that can be further elaborated toward medicinally relevant building blocks or natural products.

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