29539-19-3

Upstream product

• 87-41-2 2-benzofuran-1(3H)-one 
• 618-31-5 benzylidene dibromide 
• 7695-69-4 bis(phenylthio)methylbenzene 
• 13141-40-7 [2-(2-phenylethynyl)phenyl]methanol 
• 536-74-3 phenylacetylene 
• 59046-72-9 o-(phenylethynyl)benzaldehyde 
• 64-17-5 ethanol 
• 5159-41-1 2-iodobenzyl alcohol 
• 18982-54-2 o-bromobenzyl alcohol 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 6630-33-7 ortho-bromobenzaldehyde 
• 138695-53-1 (E)-1-benzylidene-1,3-dihydroisobenzofuran 

Downstream Products

• 1448449-94-2 1-(4-((Z)-((Z)-3-benzylideneisobenzofuran-1(3H)-ylidene)methyl)phenyl)piperidine 
• 1448450-21-2 2-phenyl-3-(4-(piperidin-1-yl)phenyl)isoquinolin-1(2H)-one 
• 1448449-96-4 4-(4-((Z)-((Z)-3-benzylideneisobenzofuran-1(3H)-ylidene)methyl)phenyl)morpholine 
• 1448450-22-3 3-(4-morpholinophenyl)-2-phenylisoquinolin-1(2H)-one 
• 1448449-98-6 (1Z,3Z)-1-benzylidene-3-(3,4-dimethoxybenzylidene)-1,3-dihydroisobenzofuran 
• 1448450-23-4 3-(3,4-dimethoxyphenyl)-2-phenylisoquinolin-1(2H)-one 
• 1448450-00-7 4-((Z)-((Z)-3-benzylideneisobenzofuran-1(3H)-ylidene)methyl)-N,N-dimethylaniline 
• 1448450-37-0 C₁₅H₁₁⁽²⁾HO 
• 1448450-15-4 3-(4-isopropylphenyl)-2-phenylisoquinolin-1(2H)-one 
• 1448450-17-6 3-(4-(methylthio)phenyl)-2-phenylisoquinolin-1(2H)-one 
• 1448450-24-5 2-phenyl-3-(3,4,5-trimethoxyphenyl)isoquinolin-1(2H)-one 
• 1448449-88-4 (1Z,3Z)-1-benzylidene-3-(4-methoxybenzylidene)-1,3-dihydroisobenzofuran 
• 14959-70-7 3-(4-methoxyphenyl)-2-phenylisoquinolin-1(2H)-one 
• 14959-62-7 2-phenyl-3-phenylisoquinolin-1-one 

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.

Palladium-Catalyzed Copper-Free Sonogashira Coupling of 2-Bromoarylcarbonyls: Synthesis of Isobenzofurans via One-Pot Reductive Cyclization

Palladium-catalyzed copper-free Sonogashira coupling of 2-bromocarbonyls is presented. This method afforded the 2-alkynylaryl carbonyls, useful synthons for the accomplishment of many carbocyclic and heterocyclic motifs. Significantly, the strategy was extended to the one-pot synthesis of isobenzofurans via reduction followed by intramolecular 5- exo -dig cyclization.

Synthesis of dihydroisobenzofurans via palladium-catalyzed sequential alkynylation/annulation of 2-bromobenzyl and 2-chlorobenzyl alcohols under microwave irradiation

The palladium-catalyzed synthesis of dihydroisobenzofurans has been performed by sequential Sonogashira cross-coupling/cyclization reactions between terminal alkynes and 2-(hydroxymethyl)bromoand chlorobenzenes in methanol as solvent at 130 °C under microwave irradiation. A 4,4'-dichlorobenzophenone oxime-derived chloro-bridged palladacycle is an efficient pre-catalyst to perform this tandem process using 2-dicyclohexylphosphanyl-2',4',6'-triisopropylbiphenyl (Xphos) as ancillary ligand and potassium hydroxide as base in the absence of a copper cocatalyst. Under these conditions, functionalized 2-bromo- and 2-chlorobenzaldehydes are also suitable partners in the domino process affording phthalans in good yields. All the reactions can be performed under air and employing reagentgrade chemicals under low loading conditions (1 mol% Pd).

Selective cyclization of alkynols and alkynylamines catalyzed by potassium tert-butoxide

Potassium tert-butoxide (t-BuOK) was found to be an effective catalyst for the cyclization of aromatic alkynols and alkynylamines. In the presence of 10 mol % t-BuOK, a range of alkynols were converted to the corresponding exo-cyclic enol ethers as pure Z

Alkaline earth catalysis of alkynyl alcohol hydroalkoxylation/cyclization

Heavier alkaline earth bis(trimethylsilyl)amides [Ae{N(SiMe 3)2}2]2 (Ae = Ca, Sr, Ba) are shown to act as effective precatalysts for the regioselective intramolecular hydroalkoxylation/cyclization of a wide range of alkynyl and allenyl alcohols. In the majority of cases, cyclization of alkynyl alcohols produces mixtures of the possible endo- and exocyclic enol ether products, rationalized as a consequence of alkynylalkoxide isomerization to the corresponding allene derivatives. Cyclization rates for terminal alkynyl alcohols were found to be significantly higher than for substrates bearing internal alkynyl substituents, while the efficacy of cyclization was in general found to be determined by a combination of stereoelectronic influences and the thermochemical viability of the specific alkaline earth metal catalysis, which we suggest is determined by the individual M-O bond strengths. Kinetic studies have provided a rate law pertaining to a pronounced catalyst inhibition with increasing [substrate], indicating that turnover-limiting insertion of C-C unsaturation into the M-O bond requires the dissociation of substrate molecules away from the Lewis acidic alkaline earth center.

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.]

Efficient copper-catalyzed cross-coupling reaction of alkynes with aryl iodides

A copper-catalyzed cross-coupling reaction of alkynes with aryl iodides is described. The system, tolerates a broad range of functional groups and enables the use of sterically demanding substrates with only 1.0-2.5 mol-% of Cu 2O and 1.0-2.5 mol-% of xantphos as the catalyst.

Regioselective synthesis of phthalans via Cu(OTf)2-catalyzed 5-exo-dig intramolecular hydroalkoxylation of 2-(ethynyl)benzyl alcohols

An efficient, regioselective Cu(OTf)2-catalyzed 5-exo-dig intramolecular hydroalkoxylation of 2-(ethynyl)benzyl alcohol, which provides a concise access to functionalized phthalan in high yields has been developed. A wide range of substrates po

Selective base-promoted synthesis of dihydroisobenzofurans by domino addition/annulation reactions of ortho-alkynylbenzaldehydes

Synthesis of the dihydroisobenzofuran nucleus was achieved by the base-promoted tandem nucleophilic addition/annulation reaction of ortho-alkynylbenzaldehydes in the presence of methanol. The reactions of aryl-, trimethylsilyl- and diethoxymethyl-substituted alkynylbenzaldehydes occurred with complete regioselectivity in good to excellent yields under microwave irradiation. The reactions of alkyl-substituted alkynylbenzaldehydes took place with good yields and high regioselectivity only when performed at room temperature and in the presence of a catalytic amount of a gold(III) salt. Plausible reaction mechanisms involved are discussed. The effect of the substituent at the alkynyl terminus on the cyclisation mode was tentatively rationalised. Georg Thieme Verlag Stuttgart · New York.

Versatile synthesis of (Z)-1-alkylidene-1,3-dihydroisobenzofurans and 1H-isochromenes by palladium-catalyzed cycloisomerization of 2-alkynylbenzyl alcohols

An easy synthesis of (Z)-1-alkylidene-1,3-dihydroisobenzofurans and 1H-isochromenes by palladium-catalyzed cycloisomerization of readily available 2-alkynylbenzyl alcohols under neutral conditions is reported. Reactions were carried out at 70-100°C in the