1402452-23-6

Upstream product

• 99-91-2 para-chloroacetophenone 
• 20718-17-6 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-1-phenylethan-1-one 
• 177750-13-9 N-(1-(4-fluorophenyl)vinyl)acetamide 
• 102921-26-6 (1,2-dibromoethyl)benzene 
• 16717-64-9 1-azidostyrene 
• 536-74-3 phenylacetylene 
• 100-42-5 styrene 
• 1487303-05-8 1-(4-fluoro-2-(1-phenylethynyl)phenyl)ethan-1-one 
• 1006-39-9 1-(2-bromo-4-fluorophenyl)ethanone 
• 896885-34-0 1-(4-fluorophenyl)ethan-1-one-O-acetyl oxime 
• 59142-68-6 2-bromo-4-fluorobenzaldehyde 
• 1402452-36-1 6-fluoro-3-phenylisoquinoline 2-oxide 
• 67-68-5 dimethyl sulfoxide 

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.).

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.

Palladium-Catalyzed C-H Functionalization of Aromatic Oximes: A Strategy for the Synthesis of Isoquinolines

An efficient strategy for synthesis of isoquinolines via Pd(II)-catalyzed cyclization reaction of oximes with vinyl azides or homocoupling of oximes is reported. Oximes could serve as a directing group and an internal oxidant in the transformation. This reaction features good functional group tolerance and provides a useful protocol for the synthesis of different kinds of isoquinolines under mild conditions. Some control experiments and 15N isotope labeling experiments were conducted for the mechanistic research. (Chemical Equation Presented).

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.

Gold-Catalyzed Ammonium Acetate Assisted Cascade Cyclization of 2-Alkynylarylketones

An ammonium acetate assisted gold-catalyzed cascade cyclization reaction of 2-alkynylarylketones is described. Under the reported conditions, a gold-catalyzed intramolecular cyclization of 2-alkynylarylketones takes place through two competing reaction mechanisms?-?a 5-exo-dig or a 6-endo-dig cyclization-leading to two regioisomeric intermediates: isobenzofuranium or isobenzopyrylium. In the presence of ammonium acetate, the two intermediate compounds undergo further rearrangement to 2,3-disubstituted indenones and 1,3-disubstituted isoquinolines, respectively. While both reaction pathways proceed via a cyclization-rearrangement cascade, the gold-mediated 5-exo-dig process is especially notable, as it provides a novel cyclization protocol of 2-alkynylarylketones.

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