1177408-18-2

Upstream product

• 119-65-3 isoquinoline 
• 459-57-4 4-fluorobenzaldehyde 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 1532-72-5 isoquinoline N-oxide 
• 2251-76-5 2-(4-fluorophenyl)-2-oxoacetic acid 
• 140-75-0 para-fluorobenzylamine 
• 5153-69-5 4-fluoro-β-nitrostyrene 
• 1647-49-0 2-(p-fluorobenzoyl)-1,2-dihydroisoquinaldonitrile 
• 1198-30-7 1-isoquinolinecarbonitrile 
• 460-00-4 1-Bromo-4-fluorobenzene 

Relevant academic research and scientific papers

The synergistic effect of self-assembly and visible-light induced the oxidative C-H acylation of N-heterocyclic aromatic compounds with aldehydes

Constructing carbon-carbon bonds through oxidative cross-coupling between two hydrocarbon compounds is regarded as a foundational issue in green chemistry. High atom-economy and mild conditions are long term pursued goals in this field. Herein, we develop

Minisci aroylation of N-heterocycles using choline persulfate in water under mild conditions

Metal persulfate mediated thermal oxidative organic transformations invariably require a higher temperature and frequently use an organic solvent. The objective of this work was to develop persulfate mediated oxidative transformations that can be performed nearly at room temperature using water as a solvent. This report describes modified Minisci aroylation of isoquinolines with arylglyoxylic acids using choline persulfate and its pre-composition (choline acetate and K2S2O8) in water at 40 °C. A few other nitrogen heterocycles were also utilized affording various aroylated products in good to excellent yields. Unlike metal persulfate that could produce metal salt byproducts, a key feature of the chemistry reported herein includes the use of environmentally benign choline persulfate containing biodegradable choline as a counter-cation, the Minisci reaction demonstrated at 40 °C in water as the only solvent, and unconventional activation of persulfate. This journal is

Room Temperature Metal-Catalyzed Oxidative Acylation of Electron-Deficient Heteroarenes with Alkynes, Its Mechanism, and Application Studies

Herein, we report an original one-step, simple, room-temperature, regioselective Minisci reaction for the acylation of electron-deficient heteroarenes with alkynes. The method has broad functional group compatibility and gives exclusively monoacylated products in good to excellent yields. The mechanistic pathway was analyzed based on a series of experiments confirming the involvement of a radical pathway. The 18O-labeling experiment suggested that water is a source of oxygen in the acylated product, and head space GC-MS experiment shows the C-C cleavage occurs via release as CO2.

Acyl Radicals from Terminal Alkynes: Photoredox-Catalyzed Acylation of Heteroarenes

A photoredox-mediated acylation reaction of electron deficient heteroarenes with terminal alkynes is reported. The method relies on oxidative cleavage of phenylacetylenes for generation of acyl radicals as a key enabling feature. The reaction is regiosele

Oxidant-Controlled C-sp2/sp3-H Cross-Dehydrogenative Coupling of N-Heterocycles with Benzylamines

Oxidant controlled ionic liquid mediated cross-dehydrogenative coupling (CDC) of benzylamines with N-heterocycles having sp2 or sp3 carbon resulted in the formation of C-benzoylated or alkenylated products. Benzoylation of N-heterocycles occurs via (NH4)2S2O8 catalyzed benzoyl radical formation. An oxidative alkenylation of N-heterocycles having C-sp3 carbon (2-methylaza-arenes) occurs via deamination of benzylamine followed by C-sp3-H bond activation in high stereoselectivity. Both benzoylation and alkenylation protocols are metal-free, green, simple, efficient, and tolerate a wide variety of functional groups.

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.

TBHP/TFA mediated oxidative cross-dehydrogenative coupling of N-heterocycles with aldehydes

An effective and metal-free oxidative cross-dehydrogenative coupling (CDC) of N-heterocycles with diverse aldehydes has been established in the presence of TBHP/TFA. The scope with respect to aldehyde and N-heterocycle components is broad, allowing facile synthesis of a broad range of structurally diverse C1-acyl substituted heterocycles in good efficiency.

Synthesis of heterocyclic monomers via Reissert chemistry

The chemistry of Reissert compounds has been used to synthesize activated difluorotetraketone monomers containing two coupled isoquinolyl moieties, linked at either the 1,1'-or 4,4'-positions. These monomers offer routes to novel families of poly(heteroarylene ether)s. New 4,4'-coupled bis(Reissert compound) 9 containing 4,4'-diketo moieties failed to afford the desired difluorotetraketo monomer upon attempted rearrangement. However, analogous bis(Reissert compound) 19 containing 4,4'-dibenzyl units did so, via aldehyde condensation, hydrolysis of the intermediate ester and oxidation of the four benzylic moieties to keto groups; thus the novel difluorotetraketone monomer 10 was prepared. Novel bis(Reissert compound)s 24, 28, and 35 were synthesized from diacid chlorides and 4-(pfluorobenzyl)isoquinoline. Rearrangement of 24 to the diketone 29, followed by oxidation of the 4-benzyl moieties resulted in difluorotetraketone monomer 30 containing a 1,1'-linked bisisoquinoline. The 1,1'-linked bis(isoquinolylfluorodiketo) monomer 38, isomeric with 10, was prepared from 4-(p-fluorobenzyl) Reissert compound 36 by condensation with terephthaldehyde, ester hydrolysis to diol 37, and oxidation. In the course of this effort, a number of new isoquinoline Reissert compounds were synthesized as model systems.

Synthesis of quinolinyl and isoquinolinyl phenyl ketones as novel agonists for the cannabinoid CB2 receptor

A series of quinolinyl and isoquinolinyl phenyl ketones was synthesized and their CB2 receptor-dependent G-protein activities were determined using the [35S]GTPγS binding assay. Both quinoline and isoquinoline derivatives exhibited similar CB2 receptor agonist activity, the most potent ligands being the 2-(Me2N)-phenyl substituted derivatives, which were also full agonists at the CB2-receptor.