1199554-67-0

Upstream product

• 1199554-66-9 2-[2-(3-hydroxyphenyl)-1-ethynyl]benzaldehyde 
• 74-88-4 methyl iodide 
• 768-70-7 1-ethynyl-3-methoxybenzene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 2398-37-0 3-methoxyphenyl bromide 
• 38846-64-9 2-ethynylbenzaldehyde 
• 766-85-8 3-methoxy-1-iodobenzene 
• 77123-58-1 2-[2-(trimethylsilyl)ethynyl]benzaldehyde 

Downstream Products

• 1199554-84-1 (3-methoxyphenyl)(3-phenyl-1-naphthyl)methanone 
• 1226977-89-4 6-(3-methoxyphenyl)-11bH-isoquinolino[2,1-a]pyrrolo[2,1-c]quinoxaline 
• 1361106-91-3 C₂₃H₂₀N₂O₃S 
• 1389315-60-9 2-benzyl-4-bromo-3-(3-methoxyphenyl)isoquinolin-1(2H)-one 
• 56383-91-6 3-(3-methoxyphenyl)-1H-isochromen-1-one 
• 134949-02-3 3-(3-methoxyphenyl)isoquinoline 
• 1403583-63-0 6-(3-methoxyphenyl)-10-methylbenzo[4,5]imidazo[2,1-a]isoquinoline 

Relevant academic research and scientific papers

Facile preparation of 3-aryl-4-iodoisoquinolines from N-(o-Arylethynyl)benzyl p-toluenesulfonamides with iodine and base

Treatment of N-(o-arylethynyl)benzyl p-toluenesulfonamides with molecular iodine in the presence of NaHCO3 at 60 °C, followed by the reaction with tBuOK at room temperature gave 3-aryl-4-iodoisoquinolines in good yields. 4-Iodo-3-phenylisoquinoline, which is one of the obtained 3-aryl-4-iodoisoquinolines, was further transformed into isoquinoline derivatives smoothly. The present approach is a novel one-pot method for the preparation of 3-aryl-4-iodoisoquinolines from N-(o-arylethynyl)benzyl p-toluenesulfonamides under transition-metal-free conditions.

One-pot Synthesis of Isoquinoline-Fused Isoquinolines via Intramolecular Hydroamination/Aza-Claisen Type Rearrangement Cascade

A one-pot, two-step synthesis of isoquinoline-fused isoquinolines from α-amino acid esters and 2-alkynyl benzaldehydes are reported. The strategy comprises an unconventional Pictet-Spengler reaction between α-amino acid esters and 2-alkynyl benzaldehydes to give isoquinoline intermediates. Subsequent gold-catalyzed intramolecular hydroamination furnishes isoquinoline-fused isoquinolines. The scope of this strategy is further extended to prepare multisubstituted isoquinoline-fused isoquinolines via subjecting the N-allylated isoquinoline intermediates to gold-catalyzed intramolecular hydroamination followed by aza-Claisen type rearrangement. (Figure presented.).

Modular synthesis of 3-substituted isocoumarinsviasilver-catalyzed aerobic oxidation/6-endoheterocyclization ofortho-alkynylbenzaldehydes

A method involving silver-catalyzed aerobic oxidation/6-endoheterocyclization ofortho-alkynylbenzaldehydes to yield 3-substituted isocoumarins is described. The developed protocol allows convenient access to a range of synthetically useful 3-substituted isocoumarins and related fused heterocyclolactones in good to high yields, using silver tetrafluoroborate as the catalyst, and atmospheric oxygen as the terminal oxidant and the source of endocyclic oxygen. Mechanistic studies suggest the involvement of a free-radical pathway.

Catalytic Asymmetric Tandem Reaction of o-Alkynylbenzaldehydes, Amines, and Diazo Compounds

An efficient asymmetric tandem reaction of o-alkynylbenzaldehydes, amines, and diazo compounds catalyzed by chiral silver imidodiphosphate has been established. Chiral 1,2-dihydroisoquinoline analogues have a tertiary stereocenter at the C1 position, and substituents at the C3 position are available with up to 97% yields and 98% ee. These products can be elaborated into the corresponding β-aminophosphonates or PARP1-inhibitor analogues.

Catalytic asymmetric three-component reaction of 2-alkynylbenzaldehydes, amines, and dimethylphosphonate

An efficient enantioselective synthesis of cyclic α-aminophosphonates via multicomponent reactions of 2-alkynylbenzaldehydes, amines, and dimethylphosphonate has been developed with the use of a chiral silver spirocyclic phosphate as the catalyst. This protocol provides straightforward access to a series of chiral C1-phosphonylated 1,2-dihydroisoquinoline derivatives with high yields (up to 99%) and high enantioselectivities (up to 94% ee) for a broad substrate scope. The products could be further transformed into densely functionalized compounds and corresponding α-aminophosphonic acids.

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.

Silver-Catalyzed Sequential Cascade Reaction of Isocyanides with 1-(2-Ethynyl-phenyl)-prop-2-yn-1-ol: Access to Benzo[b]fluorenes and Benzofuran-Pyrroles

A silver-catalyzed cycloaromatization of 1-(2-ethynyl-phenyl)-prop-2-yn-1-ol with isocyanides efficiently provides benzo[b]fluorene and benzofuran-pyrrole derivatives through a modular cascade reaction that includes a nucleophilic attack on the diyne substrate. A C?C cross-coupling/oxygen transportation/Diels-Alder/hydrogen shift/isomerization cascade mechanistic pathway is proposed. (Figure presented.).

Vinylogous Nicholas reactions in the synthesis of bi- and tricyclic cycloheptynedicobalt complexes

The Lewis acid mediated intramolecular Nicholas reactions of allylic acetate enyne-Co2(CO)6 complexes afford cycloheptenyne-Co2(CO)6 complexes in three manifestations. Electron rich aryl substituted alkyne complexes give tricyclic 6,7,x-benzocycloheptenyne complexes, with x = 5, 6, or 7. Allylsilane substituted complexes afford exo methylene bicyclic x,7-cycloheptenyne complexes (x = 6,7). The allyl acetate function may also be replaced by a benzylic acetate, to afford dibenzocycloheptyne-Co2(CO)6 complexes. Following reductive complexation, the methodology may be applied to the synthesis of the icetexane diterpene carbon framework.

Insights into the Gold-Catalyzed Propargyl Ester Rearrangement/Tandem Cyclization Sequence: Radical versus Gold Catalysis - Myers-Saito- versus Schmittel-Type Cyclization

A detailed study of the gold-catalyzed tandem 1,3-carboxy migration/allene-enyne cycloisomerization was undertaken. It was found that after the initial allene formation the selectivity of the reaction is strongly influenced by the polarization of the remaining alkyne. Depending on the substitution pattern of the starting diynes, either a Schmittel- or a Myers-Saito-type cyclization was triggered. The 6-endo-dig Myers-Saito-type cyclization gave access to benzo[b]fluorenes, while the Schmittel pathway (5-exo-dig) delivered benzofulvenes as final products. In special cases a yet unknown pathway was opened by the ambiphilic nature of the allene moiety. In these cases completely different products were obtained by the nucleophilic attack of the alkyne moiety onto the allene that can also act as an electrophile. Mechanistic studies revealed that diradical pathways can be ruled out for this type of tandem cyclization reactions and it is shown that both steps of the reaction cascade are catalyzed by the gold complex.

Silver-catalyzed domino hydroarylation/cycloisomerization reactions of ortho-alkynylbenzaldehydes: An entry to functionalized isochromene derivatives

A Ag-catalyzed versatile and efficient access to 1H,1-arylisochromenes is reported. Starting from ortho-alkynylbenzaldehydes bearing various substitution patterns on the benzaldehyde and alkynyl units, the use of silver triflate (10 mol %) allowed a domino hydroarylation/cycloisomerization reaction process, leading to aryl-functionalized 1H-isochromene (>10 compounds, 80-98% yields). Notably, the reaction conditions were also compatible with benzaldehydes bearing an aliphatic-substituted alkynyl moiety with modest to good yields (34-88%, 10 compounds).