1402452-25-8

Upstream product

• 536-74-3 phenylacetylene 
• 16717-64-9 1-azidostyrene 
• 92574-04-4 p-methoxyacetophenone-N-acetylhydrazone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 102921-26-6 (1,2-dibromoethyl)benzene 
• 20718-17-6 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-1-phenylethan-1-one 
• 177750-10-6 N-(1-(4-methoxy)phenylethyl)acetamide 
• 96155-57-6 1-(4-methoxyphenyl)ethanone O-acetyl oxime 
• 43192-31-0 2-bromo-4-methoxybenzaldehyde 
• 1402452-38-3 6-methoxy-3-phenylisoquinoline 2-oxide 
• 67-68-5 dimethyl sulfoxide 
• 1286747-88-3 4-methoxy-2-(phenylethynyl)benzaldehyde oxime 
• 1251832-84-4 2-(2-phenylethynyl)-4-methoxybenzaldehyde 
• 82664-05-9 hydrazon obtained by condensation of 2-pyridylhydrazine with p-methoxyacetophenone 

Relevant academic research and scientific papers

Synthesis method of 1, 3-disubstituted isoquinoline derivative

The invention discloses a synthesis method of a 1, 3-disubstituted isoquinoline derivative, which comprises the steps of adding an enamine compound, a sulfoxide ylide compound and a dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer into an organic solvent, heating under a nitrogen condition to react, and after the reaction is completed, performing post-treatment to obtain the 1, 3-disubstituted isoquinoline compound. According to the method, the 1, 3-disubstituted isoquinoline derivative is synthesized in one step through simple and easily available raw materials, the conversion efficiency is high, and the atom economy is good; and meanwhile, the method is simple to operate, high in reaction yield and wide in substrate adaptability.

Rhodium(iii)-catalyzed annulation of enamides with sulfoxonium ylides toward isoquinolines

An efficient rhodium(iii)-catalyzed C-H activation followed by intermolecular annulation between enamides and sulfoxonium ylides has been developed. The transformation proceeds smoothly with a broad range of substrates, affording a series of isoquinoline derivatives in moderate to good yields under additive-free conditions.

Synthesis of Isoquinoline Derivatives via Palladium-Catalyzed C?H/C?N Bond Activation of N-Acyl Hydrazones with α-Substituted Vinyl Azides

A palladium-catalyzed cyclization of N-acetyl hydrazones with vinyl azides has been developed. Various substituted isoquinolines, including diverse fused isoquinolines can be prepared via this protocol in moderate to good yields. Mechanistic studies suggest that α-substituted vinyl azide serves as an internal nitrogen source. Also, C?H bond activation and C?N bond cleavage have been realized using hydrazone as directing group. (Figure presented.).

Manganese-Catalyzed Carbonylative Annulations for Redox-Neutral Late-Stage Diversification

An inexpensive, nontoxic manganese catalyst enabled unprecedented redox-neutral carbonylative annulations under ambient pressure. The manganese catalyst outperformed all other typically used base and precious-metal catalysts. The outstanding versatility o

Bidentate Directing-Enabled, Traceless Heterocycle Synthesis: Cobalt-Catalyzed Access to Isoquinolines

Traceless heterocycle synthesis based on transition-metal-catalyzed C-H functionalization is synthetically appealing but has been realized only in monodentate directing systems. Bidentate directing systems allow for the achievement of high catalytic reactivity without the need for a high-cost privileged ligand. The first bidentate directing-enabled, traceless heterocycle synthesis is demonstrated in the cobalt-catalyzed synthesis of isoquinolines via 2-hydrazinylpyridine-directed C-H coupling/cyclization with alkynes. Convenient directing group installation through a ubiquitously present ketone group allows synthetic elaboration for complex molecules.

Cp?CoIII Catalyzed Site-Selective C-H Activation of Unsymmetrical O-Acyl Oximes: Synthesis of Multisubstituted Isoquinolines from Terminal and Internal Alkynes

The synthesis of isoquinolines by site-selective C-H activation of O-acyl oximes with a Cp?CoIII catalyst is described. In the presence of this catalyst, the C-H activation of various unsymmetrically substituted O-acyl oximes selectively occurred at the sterically less hindered site, and reactions with terminal as well as internal alkynes afforded the corresponding products in up to 98% yield. Whereas the reactions catalyzed by the Cp?CoIII system proceeded with high site selectivity (15:1 to 20:1), use of the corresponding Cp?RhIII catalysts led to low selectivities and/or yields when unsymmetrical O-acyl oximes and terminal alkynes were used. Deuterium labeling studies indicate a clear difference in the site selectivity of the C-H activation step under Cp?CoIII and Cp?RhIII catalysis. Isoquinolines are obtained by the C-H activation of O-acyl oximes with a Cp?CoIII catalyst. Whereas the reactions catalyzed by the Cp?CoIII system proceed with high site selectivity favoring C-H activation at the sterically less hindered site, the use of the corresponding Cp?RhIII catalyst leads to low selectivities and/or yields when unsymmetrical O-acyl oximes and terminal alkynes are used.

Preparation of 1-methyl-3-phenylisoquinoline derivatives from oximes using polyphosphoric esters

We show a beneficial new approach to the preparation of 1-methyl-3-phenylisoquinoline derivatives. This method involves heating polyphosphate ester and the appropriate oximes obtained from 3,4-diphenylbut-3-en-2-one derivatives. The isoquinolines were syn

Palladium-catalyzed C-H oxidation of isoquinoline N-oxides: Selective alkylation with dialkyl sulfoxides and halogenation with dihalo sulfoxides

A novel palladium-catalyzed C-H oxidation of isoquinoline N-oxides has been developed for regioselectively synthesizing substituted isoquinolines. The method represents the first example of using dialkyl sulfoxides as the alkyl sources for the construction of 1-alkylated isoquinolines. Moreover, the regioselective halogenation of isoquinoline N-oxides is also successful using dihalo sulfoxides as the halide sources. Copyright