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Synthesis method of acylated quinoline or isoquinoline derivative

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£º
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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Palladium(II)-catalyzed C-C and C-O bond formation for the synthesis of C1-benzoyl isoquinolines from isoquinoline: N -oxides and nitroalkenes

C1-Benzoyl isoquinolines can be generated via a palladium(ii)-catalyzed C-C and C-O coupling of isoquinoline N-oxides with aromatic nitroalkenes. The reaction proceeds through remote C-H bond activation and subsequent intramolecular oxygen atom transfer (OAT). In this reaction, the N-O bond was designed as a directing group in the C-H bond activation as well as the source of an oxygen atom.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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In Situ Generation of Quinolinium Ylides from Diazo Compounds: Copper-Catalyzed Synthesis of Indolizine

The Cu-catalyzed three-component reaction between quinolines, diazo compounds, and alkenes has been established for direct construction of indolizine derivatives via quinolinium ylides. This methodology is distinguished by the use of a commercially inexpensive catalyst and readily available starting materials, wide substrate scope, and operational simplicity.

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Reference£º
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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Three-Component Minisci Reaction with 1,3-Dicarbonyl Compounds Induced by Visible Light

A three-component Minisci reaction coupling of 1,3-dicarbonyl compounds with vinyl ethers and quinolines or isoquinolines under visible light is developed. The 1,3-dicarbonyl compound undergoes single-electron oxidation to afford an electrophilic 1,3-dicarbonyl radical under visible light irradiation. Due to the polarity of the free radical, the electrophilic radical adds to the electron-rich olefin to afford the nucleophilic radical. It coupled with the heteroarene to afford the three-component coupling products.

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Reference£º
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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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,
Isoquinoline | C9H7N – PubChem

 

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Chiral silanediols in anion-binding catalysis

A perfect pair: Silanediols are effective catalysts for the addition of silyl ketene acetals to N-acylisoquinolinium ions. Importantly, this is the first example of a silanediol plausibly participating in anion-binding catalysis, a relatively new direction in the field of hydrogen-bond-donor catalysis. The chiral, enantiopure C2-symmetric silanediol 1 catalyzes enantioselective transformations. Copyright

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Reference£º
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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Metal-Free Oxidative B?N Coupling of nido-Carborane with N-Heterocycles

A general method for the oxidative substitution of nido-carborane (7,8-C2B9H12?) with N-heterocycles has been developed by using 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) as an oxidant. This metal-free B?N coupling strategy, in both inter- and intramolecular fashions, gave rise to a wide array of charge-compensated, boron-substituted nido-carboranes in high yields (up to 97 %) with excellent functional-group tolerance under mild reaction conditions. The reaction mechanism was investigated by density-functional theory (DFT) calculations. A successive single-electron transfer (SET), B?H hydrogen-atom transfer (HAT), and nucleophilic attack pathway is proposed. This method provides a new approach to nitrogen-containing carboranes with potential applications in medicine and materials.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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Direct Arylation of Unactivated Alkanes with Heteroarenes by Visible-Light Catalysis

The functionalization of aliphatic C-H bonds is both a major challenge and a desirable goal in organic synthesis. Here, we describe the successful arylation of unactivated alkanes with heteroarenes by using iridium polypyridyl complexes as the photocatalyst and persulfate as the HAT catalyst precursor under visible-light irradiation. This reaction features good functional group tolerance and broad scope with regard to both alkane and heteroarene substrates (37 examples), which allows direct access to alkyl-substituted N-heteroarenes, a key structural motif in natural products and bioactive molecules.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem