1383549-86-7

Upstream product

• 766-98-3 1-ethynyl-4-fluorobenzene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 18904-38-6 N-benzyl-2-pyridinecarboxamide 
• 100-46-9 benzylamine 
• 212505-57-2 N-(2-iodobenzylidene)-2-methylpropan-2-amine 
• 318-49-0 2-(4-fluorobenzyl)isoindoline-1,3-dione 
• 85-44-9 phthalic anhydride 
• 140-75-0 para-fluorobenzylamine 
• 193675-43-3 N-(4-fluorobenzylidene)-4-methylbenzenesulfonamide 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 26260-02-6 2-iodobenzaldehyde 
• 50624-28-7 1-(isoquinolin-2(1H)-yl)ethan-1-one 
• 1765-93-1 4-fluoroboronic acid 
• 119-65-3 isoquinoline 

Relevant academic research and scientific papers

Silver/Rhodium Relay Catalysis Enables C?H Functionalization of In Situ Generated Isoquinolines with Sulfoxonium Ylides: Construction of Hexahydrodibenzo[a,g]quinolizine Scaffolds

Employing silver/rhodium relay catalysis strategy, an intramolecular electrophilic cyclization and C?H activation followed by cascade hydrogenation and reductive amination has been developed. The acylmethylated isoquinoline derivatives could be afforded with broad substrate scope in 23–88% yields, which could be further transformed to the core skeleton of hexahydrodibenzo[a,g]quinolizine as drug-candidates. Moreover, this reaction was achieved in a gram-scale. A reasonable reaction mechanism has been proposed based on a series of control and KIE experiments. (Figure presented.).

NHC-Mediated Stetter-Aldol and Imino-Stetter-Aldol Domino Cyclization to Naphthalen-1(2 H)-ones and Isoquinolines

N-Heterocyclic carbene-catalyzed tandem Stetter-aldol reaction of phthalaldehyde and α,β-unsaturated ketimines has been developed to afford functionalized naphthalen-1(2H)-one derivatives as the formal [4+2] annulation product. Interestingly, the reaction of aldimines led to the formation of isoquinoline derivatives instead of the expected indanone derivatives as a [4+1] annulation product.

Catalyst and additive free 6-endo-dig cyclization of ortho-alkynylarylaldimines in water: An environmentally friendly access to isoquinolines

A novel and sustainable route for the synthesis of isoquinoline was developed by reacting 2-ethynylbenzaldehyde with ammonium hydroxide in water. This method provides a convenient, atom-economical, and catalyst-free access to diversely substituted isoquinolines with moderate to good yields.

Method for synthesizing isoquinoline compound

The invention discloses a method for synthesizing an isoquinoline compound. The isoquinoline compound is shown in formula I, wherein R1 is hydrogen, a halogen atom, an alkyl, an alkoxy or an amino, and R2 is hydrogen, a halogen atom, an alkyl, an alkoxy or an amino. According to the invention, o-alkynyl aldehyde and p-hydroxybenzylamine are used as raw materials to synthesize a target product through series reactions of imidization, cyclization and oxidation elimination, the method for synthesizing the isoquinoline compound is simple and rapid, the yield of the target compound is high, and a necessary basis is provided for further researching the compound in formula I or related compounds.

An efficient approach to isoquinoline via AgNO3-promoted 6-endo-dig cyclization followed by oxidative elimination of o-alkynylarylaldimines and its application in fluoride recognition

A novel 6-endo-dig cyclization followed by oxidation/elimination of o-alkynylarylaldimines with 4-hydroxybenzylamine was developed for preparation of isoquinolines. The intermediates of this tandem reaction were monitored by mass spectroscopy (MS) to confirm the reaction pathway. This methodology was further applied to the design and synthesis of a novel ratiometric chemosensor for determination of fluoride.

Hydrophilic Pd-phosphines catalyzed one-pot synthesis of substituted isoquinolines, furopyridines and thienopyridines in aqueous medium

A first example of simple and efficient hydrophilic Pd-phosphine complexes catalyzed one-pot three-component reaction of ortho-bromo aldehydes, terminal alkynes and ammonium acetate proceeds through the tandem coupling-imination-annulation path for the synthesis of substituted isoquinolines, furopyridines and thienopyridines in good to excellent yields in green aqueous medium at mild temperature was described.

Highly Regioselective Isoquinoline Synthesis via Nickel-Catalyzed Iminoannulation of Alkynes at Room Temperature

A simple and cost-efficient nickel catalytic system for the annulation of 2-haloaldimines with alkynes to synthesize 3,4-disubstituted and 3-substituted isoquinolines at room temperature has been developed. The air-stable and inexpensive Ni(dppe)Cl2 was employed as a precatalyst, and Et3N was found to be an essential additive for obtaining high yields. By using this nickel catalytic system one-pot three-component direct synthesis of isoquinolines starting with simple 2-halobenzaldehydes, tert-butylamine, and alkynes were also achieved. These reactions occur in moderate to excellent yields with complete regioselectivity. Moreover, these reactions feature a broad substrate scope, easy scalability, operational simplicity, and excellent practicality.

Alkoxide-Catalyzed Hydrosilylation of Cyclic Imides to Isoquinolines via Tandem Reduction and Rearrangement

An alkoxide-catalyzed hydrosilylation of cyclic imides to isoquinolines was realized via tandem reduction and rearrangement. Using TMSOK as the catalyst and (EtO)2MeSiH as the reductant, a series of cyclic imides containing different functional groups were reduced to the corresponding 3-aryl isoquinolines in moderate to good yields. The scenario of the reaction pathway was supposed to involve the reduction of imides to ω-hydroxylactams, which underwent rearrangement in the presence of a base catalyst, and then the carbonyl reduction, followed by siloxy elimination.

One substrate, two modes of C-H functionalization: A metal-controlled site-selectivity switch in C-H arylation reactions

A unique site-selectivity switch has been achieved in the ruthenium-catalyzed C-H arylation reaction of N-acetyl-1,2-dihydroisoquinolines. This metal-mediated switch is antipodal to the previous report on the palladium-mediated C-4 C-H arylation on the same substrate. Mechanistic details reveal interesting aspects of the reaction pathway, and kinetic studies bring out the difference in the modes of C-H activation adopted by the two catalytic systems.

Cobalt-Catalyzed ortho-C?H Functionalization/Alkyne Annulation of Benzylamine Derivatives: Access to Dihydroisoquinolines

A practical picolinamide-directed C?H functionalization/alkyne annulation of benzylamine derivatives enabling access to the previously elusive 1,4-dihydroisoquinoline skeleton was developed using molecular O2 as the sole oxidant and Co(OAc)2 as precatalyst. The method is compatible with both internal and terminal alkynes and shows high versatility and functional-group tolerance. Furthermore, full preservation of enantiopurity is observed when using non-racemic α-substituted benzylamine derivatives. Kinetic analysis of the reagents and catalyst, labeling experiments, and the isolation and identification of catalytically competent Co-complexes revealed important insights about the mechanism.