83640-83-9

Upstream product

• 14174-13-1 6,7-dimethoxy-3,4-dihydro-1H-isochromen-1-one 
• 13267-99-7 6,7-dimethoxy-3,4-dihydro-1H-isochromene 
• 100-66-3 methoxybenzene 
• 123-11-5 4-methoxy-benzaldehyde 
• 7417-21-2 2-(3,4-dimethoxyphenyl)ethyl alcohol 

Downstream Products

• 102693-02-7 2-(4-methoxybenzoyl)-4,5-dimethoxyphenylacetic acid 

Relevant academic research and scientific papers

Heteropolyacid ionic liquid heterogeneously catalyzed synthesis of isochromansviaoxa-Pictet-Spengler cyclization in dimethyl carbonate

A recyclable and efficient heterogeneous, green catalyst based on the synthesis of Keggin-type polyoxometalate (H3PMo12O40) and vitamin B1 analogue 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazol-3-ium (HEMT),i.e., [HEMTH]H2[PMo12O40] was prepared. Oxa-Pictet-Spengler cyclization of arylethanols and aldehydes were catalyzed to afford various substituted isochromans in moderate conditions with excellent yields using dimethyl carbonate (DMC) as a green solvent. Furthermore, this protocol was applicable in a gram-scale reaction, and the catalyst could be recycled eight times without significant loss of activity.

Direct oxidative C(sp3)–H cyanation of secondary benzylic ethers

Current studies on the oxidative C–H functionalization of benzylic ethers for C–C forging process dominantly focus on primary ethers. The corresponding reaction of secondary ethers remains underdeveloped. Herein, a practical and efficient oxidative C–H cyanation of secondary benzylic ethers with TMSCN in the presence of DDQ is described. The metal-free process is well tolerated with a wide variety of electronically varied α-monosubstituted isochromans, facilely furnishing a library of isochromans bearing α-aryl α-cyano substituent patterns for further diversification and bioactive small molecule identification.

Synthesis of isochromans via Fe(OTf)2-catalyzed Oxa-Pictet–Spengler cyclization

Fe(OTf)2 has been found to be an efficient catalyst for the Oxa-Pictet–Spengler cyclization reaction leading to isochromans. A series of substituted isochromans were obtained with good to excellent isolated yields by coupling β-arylethanols wit

Silica-supported policresulen as a solid acid catalyst for organic reactions

A new type of solid catalyst was prepared by coating a thin layer of policresulen, an inexpensive polymer prepared via condensation of 2-hydroxy-4-methylbenzenesulfonic acid and formaldehyde that has been used as commercially available drug, onto the surface of silica. The policresulen component is insoluble in many organic solvents and can be adsorbed on silica with the aid of hydrogen bonding. The obtained silica/policresulen composite showed remarkable catalytic activity for various organic reactions. In model reactions, the catalyst can be recycled several times without significant loss of activity. The salient features of using this acid catalyst in organic reactions include cost-effectiveness, simple and time-efficient preparation, and the convenience of controlling the acid loading on the solid.

Structurally diverse α-substituted benzopyran synthesis through a practical metal-free C(sp3)-H functionalization

A trityl ion-mediated practical C-H functionalization of a variety of benzopyrans with a wide range of nucleophiles (organoboranes and C-H molecules) at ambient temperature has been disclosed. The metal-free reaction has an excellent functional group tole

Bismuth triflate as a safe and readily handled source of triflic acid: Application to the oxa-pictet-spengler reaction

The oxa-Pictet-Spengler reaction with various aldehydes and-arylethanol yields 1-substituted-isochromans in the presence of bismuth triflate as catalyst in good yields. The method was extended to O,O-acetals to afford the corresponding 1,1-disubstituted-i

Metal triflates: Efficient catalysts for oxa-pictet-spengler reaction

A screening of different metal triflates as catalysts was performed to get isochromans through an oxa-Pictet-Spengler reaction. Good to high yields were obtained for various aliphatic or aromatic aldehydes and β-arylethanols. A mechanism involving catalys

Oxa-Pictet-Spengler reaction in water. Synthesis of some (±)-1-aryl-6,7-dimethoxyisochromans

An acid catalyzed oxa-Pictet-Spengler reaction 'on water' leading to the synthesis of a variety of 1-aryl-6,7-dimethoxyisochromans is described. The aqueous chemistry is a much cleaner, efficient, cheaper and simple method for synthesis. The scope of reac

Zeolite-catalyzed simple synthesis of isochromans via the oxa-Pictet-Spengler reaction

The synthesis of isochromans via oxa-Pictet-Spengler reaction using a modified small pore size zeolite E4 as catalyst was investigated. Ersorb-4 (E4) is a clinoptylolite-type zeolite material with high silicon content. The reaction of 2-phenylethanol deri

OXIDATION OF 1-ARYL-6,7-DIMETHOXYISOCHROMANS WITH CHROMIUM(VI) OXIDE IN ACETIC ACID: A NEW SYNTHETIC PATHWAY TO 2-AROYL-4,5-DIMETHOXYBENZALDEHYDES AND 2-ACETYL-4,5-DIMETHOXYBENZOPHENONES

The oxidation of 1-aryl-6,7-dimethoxyisochromans with chromium(VI) oxide in acetic acid does not give the expected 2-aroylphenylacetic acids, but instead leads to a mixture consisting chiefly of 2-aroyl-4,5-dimethoxybenzaldehydes and of the corresponding