405198-79-0

Upstream product

• 696-62-8 para-iodoanisole 
• 10602-08-1 2-ethynylbenzyl alcohol 
• 5159-41-1 2-iodobenzyl alcohol 
• 768-60-5 4-methoxyphenylacetylen 
• 229027-92-3 {2-[2-(trimethylsilyl)ethynyl]phenyl}methanol 
• 127591-24-6 p-methoxyphenyl(triphenylphosphine)gold(I) 
• 6630-33-7 ortho-bromobenzaldehyde 
• 176910-67-1 2-(4-methoxyphenylethynyl)benzaldehyde 

Downstream Products

• 176910-67-1 2-(4-methoxyphenylethynyl)benzaldehyde 
• 29539-11-5 3-(4-methoxyphenyl)-1H-isochromene 
• 1205555-57-2 4-iodo-3-(4-methoxyphenyl)-1H-isochromene 
• 1448450-04-1 4-((Z)-((Z)-3-(4-methoxybenzylidene)isobenzofuran-1(3H)-ylidene)methyl)-N,N-dimethylaniline 
• 1620151-40-7 6a-(4-methoxyphenyl)-5,6a-dihydrobenzo[g]isochromeno[3,4-b]chromene 
• 1620151-41-8 8-bromo-10-chloro-6a-(4-methoxyphenyl)-5,6a-dihydroisochromeno[3,4-b]chromene 
• 1620151-28-1 6a-(4-methoxyphenyl)-5,6a-dihydroisochromeno[3,4-b]chromene 
• 1620151-33-8 8-methoxy-6a-(4-methoxyphenyl)-5,6a-dihydroisochromeno[3,4-b]chromene 
• 1620151-34-9 9-methoxy-6a-(4-methoxyphenyl)-5,6a-dihydroisochromeno[3,4-b]chromene 
• 1620151-35-0 10-methoxy-6a-(4-methoxyphenyl)-5,6a-dihydroisochromeno[3,4-b]chromene 
• 1620151-36-1 6a-(4-methoxyphenyl)-10-methyl-5,6a-dihydroisochromeno[3,4-b]chromene 
• 1620151-37-2 10-bromo-6a-(4-methoxyphenyl)-5,6a-dihydroisochromeno[3,4-b]chromene 
• 1620151-38-3 10-fluoro-6a-(4-methoxyphenyl)-5,6a-dihydroisochromeno[3,4-b]chromene 
• 145917-96-0 3-(4-methoxyphenyl)-2H-chromene 

Relevant academic research and scientific papers

Regio- and stereoselective intramolecular hydroalkoxylation of aromatic alkynols: an access to dihydroisobenzofurans under transition-metal-free conditions

An efficient, transition-metal-free method to synthesize dihydroisobenzofuran derivatives via intramolecular hydroalkoxylation of aromatic alkynols with the promotion of cesium carbonate has been developed. The reaction proceeds regioselectively with exclusive formation of 5-exo-dig product, and only Z-isomer of the new generated double bond is observed. This new protocol features with milder reaction conditions, more convenient operation and satisfactory selectivities.

AgSCF3/Na2S2O8-Promoted Trifluoromethylthiolation/Cyclization of o-Propargyl Arylazides/ o-Alkynyl Benzylazides: Synthesis of SCF3-Substituted Quinolines and Isoquinolines

A AgSCF3/Na2S2O8-promoted trifluoromethylthiolation/cascade cyclization of o-propargyl arylazides (or o-alkynyl benzylazides) triggered by a carbon-carbon triple bond is reported. This strategy provides the synthesis of valuable SCF3-substituted quinoline and isoquinoline systems via the construction of one C(sp2)-SCF3 bond and one C-N bond within one process.

Fused-Ring Formation by an Intramolecular “Cut-and-Sew” Reaction between Cyclobutanones and Alkynes

The development of a catalytic intramolecular “cut-and-sew” transformation between cyclobutanones and alkynes to construct cyclohexenone-fused rings is described herein. The challenge arises from the need for selective coupling at the more sterically hind

Lewis Acid Catalyzed Tandem Polycyclization of Internal Alkynols and Vinyl Azides

A novel Lewis acid catalyzed tandem cyclization reaction of internal alkynols and vinyl azides has been achieved to afford a series of products containing a pyran-based indeno[1,2-c]isochromene scaffold in moderate to high yields. This tandem polycyclization protocol provides a straightforward entry to construct the complex polycyclic skeleton through cycloisomerization, formal [4 + 2] cycloaddition, and an elimination process.

Efficient synthesis of isothiochromene derivatives by Pd-catalyzed hydrothiolation reaction

An efficient method for the preparation of isothiochromene derivatives through the palladium-catalyzed intramolecular hydrothiolation reaction of halides and thiourea is reported. Two carbon-sulfur bonds are formed in this one-pot palladium-catalyzed cascade reaction. This new protocol is free from foul-smelling thiols and operates under mild conditions to give isothiochromene derivatives in excellent yields and with excellent 6-endo-dig selectivity. Copyright

Stabilisation of carbon-supported palladium nanoparticles through the formation of an alloy with gold: Application to the Sonogashira reaction

A conceptually novel strategy based on the use of a bimetallic Pd-Au/C catalyst and its application to the Sonogashira reaction under ligand- and additive-free conditions was studied. Pd(OAc)2 and charcoal were dispersed in MeOH (100 mL). Then, hydrogen gas was bubbled through the solution for 5 min to remove the oxygen. The resulting mixture was stirred for 12 h at 25°C under H2. The catalyst was filtered under Millipore membrane washed with MeOH and dried under vacuum. ICP analyses were performed on the filtrate to verify the final Pd metal loading on carbon to be 5%wt. Detailed HR-TEM analyses established that the aggregation phenomenon can be considerably slowed down thanks to the stabilising, but catalytically inactive, gold atoms. Although X-ray photoelectron spectroscopy (XPS) analysis identified Au0 and Pd0 as the major species present in the as-prepared material, some ionic palladium (19 at.%) was also detected

Regioselective synthesis and evaluation of 3-alkylidene-1, 3-dihydroisobenzofurans as potential antidepressant agents

3-Alkylidene-1,3-dihydroisobenzofurans exhibited moderate antidepressant activity as evaluated by forced swim and tail suspension test methods. Virtual screening was carried out by docking the designed compounds into the serotonin binding sites of arabinase protein to predict the analogue binding mode of the compounds to the SSRIs. [Figure not available: see fulltext.]

Base-free palladium-catalyzed sonogashira coupling using organogold complexes

Turn to gold: An effective protocol for base-free Sonogashira coupling reactions using organogold complexes as nucleophilic partners has been developed. The palladium-catalyzed methodology offers a general synthesis of aryl-alkynes under operationally simple conditions in good to excellent yields. Copyright

A simple and mild synthesis of 1H-isochromenes and (Z)-1-alkylidene-1,3- dihydroisobenzofurans by the iodocyclization of 2-(1-alkynyl)benzylic alcohols

(Chemical Equation Presented) A variety of iodo-substituted isochromenes, dihydroisobenzofurans, and pyranopyridines are readily prepared in good to excellent yields under mild conditions by the iodocyclization of readily available 2-(1-alkynyl)benzylic a

Iodine-mediated electrophilic cyclization of 2-alkynyl-1-methylene azide aromatics leading to highly substituted isoquinolines and its application to the synthesis of norchelerythrine

The reaction of 2-alkynyl-1-methylene azide aromatics 1 with iodine and/or other iodium donors, such as the Barluenga reagent (Py2IBF 4/HBF4) and NIS, gave highly substituted cyclization products, namely, the 1,3-disubstituted 4-iodoisoquinolines 2, in good to high yields. Not only simple 2-alkynyl benzyl azides 1a-j and their substituted analogues 1k-u and 6 but also heteroaromatic analogues, including pyridine 8, pyrroles 10a-c, furane 10d, and thiophenes 10e-g, gave the corresponding isoquinoline derivatives in excellent to allowable yields. Electron-donating and electron-accepting substituents on the aromatic ring were equally tolerated, and either acidic or basic (or even neutral) reaction conditions, depending on the reactivity of the substrate, could be applied to smoothly convert the azide starting materials into the desired isoquinoline products in moderate to good yields. Limits were found only in connection with the substituent at the alkyne terminus, where electron-neutral or electron-donating substituents are clearly favored. The iodine-mediated electrophilic cyclization of 1 most probably proceeds through the iodonium ion intermediate 4 followed by nucleophilic cyclization of the azide and subsequent elimination of N2. This new methodology was successfully applied to the short synthesis of norchelerythrine.