22506-58-7

Upstream product

• 13267-99-7 6,7-dimethoxy-3,4-dihydro-1H-isochromene 
• 16002-63-4 phenylmagnesium iodide 
• 591-50-4 iodobenzene 
• 100-52-7 benzaldehyde 
• 7417-21-2 2-(3,4-dimethoxyphenyl)ethyl alcohol 

Downstream Products

• 101351-07-9 6,7-dimethoxy-4-phenylphtalazin-1(2H)-one 
• 41148-41-8 2,3-Methylbenzodiazepine-2 
• 41148-42-9 7,8-dimethoxy-1-phenyl-3,5-dihydro-4H-2,3-benzodiazepin-4-one 
• 57259-73-1 4,5-dimethoxy-2-benzoylbenzoic acid 
• 41148-49-6 2-benzoyl-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.

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

Efficient C(sp3)-H bond functionalization of isochroman by azadol catalysis

A novel organocatalytic C(sp3)-H bond functionalization of isochroman under practical conditions has been developed. In the presence of 5.0 mol % of AZADOL, the catalysis proceeded successfully with a broad range of substrates and nucleophiles in excellent yields.

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.

Organocatalytic approach for C(sp3)-H bond arylation, alkylation, and amidation of isochromans under facile conditions

A new catalytic approach for the synthesis of isochroman derivatives via direct C(sp3)-H bond arylation is described. The oxidation reaction with [bis(trifluoroacetoxy)iodo]benzene facilitates the regeneration of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in the C(sp3)-H bond arylation of isochroman. The reaction conditions can also be used for alkyl Grignard reagents and amides to afford the corresponding isochroman derivatives.

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

Synthesis of tetrahydroisoquinolines and isochromans via Pictet-Spengler reactions catalyzed by Br?nsted acid-surfactant-combined catalyst in aqueous media

Perfluorooctanesulfonic acid (PFOSA), Br?nsted acid-surfactant-combined catalyst, efficiently catalyzes the Pictet-Spengler reactions of β-arylethyl carbamate derivatives with aldehydes in water. The present reaction is accelerated by the addition of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). PFOSA in HFIP-water (10 v/v %) is also successfully applied to the oxa-Pictet-Spengler reactions of β-arylethyl alcohol compounds.

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

Design and development of 2,3-benzodiazepine (CFM) noncompetitive AMPA receptor antagonists

2,3-Benzodiazepines represent a class of heterocyclic compounds that interact with AMPA-type glutamate receptors in a noncompetitive manner. These compounds have attracted great interest for their pharmacological effects against acute and chronic neurodeg

1-aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: Novel AMPA receptor antagonists

Our previous publication (Eur. J. Pharmacol. 1995, 294, 411-422) reported preliminary chemical and biological studies of some 2,3- benzodiazepines, analogues of 1-(4-aminophenyl)-4-methyl-7,8- (methylenedioxy)-5H-2,3-benzodiazepine (1, GYKI 52466), which have been shown to possess significant anticonvulsant activity. This paper describes the synthesis of new 1-aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones and the evaluation of their anticonvulsant effects. The observed findings extend the structure-activity relationships previously suggested for this class of anticonvulsants. The seizures were evoked both by means of auditory stimulation in DBA/2 mice and by pentylenetetrazole or maximal electroshock in Swiss mice. 1-(4'-Aminophenyl)- (38) and 1-(3'-aminophenyl)-3,5-dihydro- 7,8-dimethoxy-4H-2,3-benzodiazepin-4-one (39), the most active compounds of the series, proved to be more potent than 1 in all tests employed. In particular, the ED50 values against tonus evoked by auditory stimulation were 12.6 μmol/kg for derivative 38, 18.3 μmol/kg for 39, and 25.3 μmol/kg for 1. Higher doses were necessary to block tonic extension induced both by maximal electroshock and by pentylenetetrazole. In addition these compounds exhibited anticonvulsant properties that were longer lasting than those of compound 1 and were less toxic. The novel 2,3-benzodiazepines were also investigated for a possible correlation between their anticonvulsant activities against convulsions induced by 2-amino-3-(3-hydroxy-5- methylisoxazol-4-yl)propionic acid (AMPA) and their affinities for benzodiazepine receptors (BZR). The 2,3-benzodiazepines did not affect the binding of [3H]flumazenil to BZR, and conversely, their anticonvulsant effects were not reversed by flumazenil. On the other hand the 2,3- benzodiazepines antagonized seizures induced by AMPA and aniracetam in agreement with an involvement of the AMPA receptor. In addition, both the derivative 38 and the compound 1 markedly reduced the AMPA receptor-mediated membrane currents in guinea-pig olfactory cortical neurons in vitro in a noncompetitive manner. The derivatives 25 and 38-40 failed to displace specific ligands from N-methyl-D-aspartate (NMDA), AMPA/kainate, or metabotropic glutamate receptors.