118741-66-5

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 922-67-8 propynoic acid methyl ester 
• 4519-46-4 methyl 2-bromoacrylate 

Downstream Products

• 32149-29-4 4-(4-methoxy-phenyl)-4-oxo-but-2-enoic acid methyl ester 
• 32095-86-6 (Z)-methyl 4-(4-methoxyphenyl)-4-oxobut-2-enoate 
• 1079995-58-6 C₁₈H₁₇NO₅ 
• 1401693-19-3 3-chloro-4-iodo-5-(4-methoxyphenyl)furan-2(5H)-one 
• 1401693-27-3 3-bromo-4-iodo-5-(4-methoxyphenyl)furan-2(5H)-one 
• 1401693-35-3 3,4-diiodo-5-(4-methoxyphenyl)furan-2(5H)-one 
• 1607841-96-2 4-allyl-5-(4-methoxyphenyl)furan-2(5H)-one 
• 5447-74-5 methyl 3-(4-methoxybenzoyl)propionate 

Relevant academic research and scientific papers

Synthesis of New γ-Lactams with gem-Difluorinated Side Chains

A short and efficient approach has been designed for the synthesis of new γ-lactams that feature gem-difluorinated side-chains in position 4. The key steps involve 1,4-addition of nitroalkane anions on electrophilic gem-difluoroalkenes, followed by a cascade nitro reduction-heterocyclization. This flexible strategy also allows easy introduction of substituents in positions 3 or 5.

: NBu4NPF6 promoted regioselective cascade synthesis of functionally embellished naphthofurans under acid, metal & solvent free conditions

nBu4NPF6 mediated highly regioselective synthesis of functionally embellished naphthofurans has been achieved from easily available naphthols and propargyl alcohols through a cascade benzylation, oxacyclisation (5-exo dig) and isomerization under solvent free conditions. The reaction works in a short time through dibenzyl ether formation followed by the decomposition to the carbocation to furnish the high yielding products with large substrate scope. The synthetic utility of the products is demonstrated through C(sp3)-H functionalization. In addition, we investigated selected naphthofurans for their anti-amyloidogenic properties. Preliminary studies suggest that these are excellent inhibitors for amyloid formation, a hallmark for several neurodegenerative diseases.

Synthesis of γ-acetoxy β-keto esters through regioselective hydration of γ-acetoxy-α,β-alkynoates

The Au(I)-catalyzed regioselective hydration of γ-acetoxy-α,β-acetylinic ester by the assistance of a neighboring carbonyl group has been developed. Varieties of simple primary, secondary, and tertiary γ-acetoxy-α,β-acetylinic esters, even those bearing sensitive functional group in the remote reaction sites, are selectively hydrated to the corresponding β-keto esters. The reaction tolerates a wide variety of other carboxylates, such as benzoates, propionates, acrylates, and pivalates, including chiral carboxylates with retention of the configuration. The broad substrate scope, including the derivatization of complex natural products and neutral and open air conditions, makes this atom economical approach very practical. 18O labeling experiments disclose that the oxygen transposition occurs from the carboxylate group to the triple bond, not from water.

Synthesis of β-allylbutenolides via one-pot copper-catalyzed hydroallylation/cyclization of γ-hydroxybutynoate derivatives

One-pot copper-catalyzed hydroallylation/lactone cyclization of γ-hydroxybutynoate derivatives was developed to afford β-allylbutenolides.

Synthesis of fluorenone and anthraquinone derivatives from aryl- and aroyl-substituted propiolates

Fluorenone derivatives were generated from aryl-substituted propiolates via a cobalt-catalyzed Diels-Alder reaction/DDQ-oxidation and Friedel-Crafts-type cyclization. Several functional groups are tolerated, and good to excellent overall yields (up to 89%) could be achieved. For the synthesis of anthraquinone derivatives, aroyl-substituted propiolates were applied in a zinc iodide catalyzed Diels-Alder reaction with 1,3-dienes. The subsequent DDQ oxidation and Friedel-Crafts-type cyclization led to symmetrical as well as some unsymmetrical anthraquinones in good to excellent yields of up to 87% over the three-step reaction sequence.

Synthesis of 3,4-dihalogenated furan-2-(5H)-ones by electrophilic cyclization of 4-hydroxy-2-alkynoates

Functionalized 3,4-dihalogenated furan-2(5H)-ones can be readily prepared in moderate to good yields by treating 4-hydroxy-4-arylbut-2-ynoate derivatives with ICl, IBr, and I2. Both halogen atoms of the electrophile are incorporated in the product. The resulting halides can further afford polycyclic aromatic compounds using known palladium-catalyzed coupling reactions.

Robust eco-friendly protocol for the preparation of γ-hydroxy- α,β-acetylenic esters by sequential one-pot elimination-addition of 2-bromoacrylates to aldehydes promoted by LTMP in 2-MeTHF

An efficient and widely applicable preparation of γ-hydroxy-α, β-acetylenic esters is described by means of a one-pot dehydrobromination of a 2-bromoacrylate ester with LTMP followed by the electrophilic addition of the transient propiolate to different aldehydes in the eco-friendly solvent 2-MeTHF. The Royal Society of Chemistry 2012.

A mild method for the preparation of γ-hydroxy-α,β- acetylenic esters

The beauty of silver has been demonstrated in the alkynylation of functionalized aldehydes and ketones. Silver acetylides of alkynyl propiolates undergo addition to carbonyl compounds in the presence of [Cp 2ZrCl2] and AgOTf (see scheme) in a reaction that is compatible with both base-sensitive and acid-sensitive functional groups. Tf = trifluoromethanesulfonyl.

Propiolophenone derivatives

Propiolophenone derivatives of the formula STR1 wherein R6 is hydrogen, lower alkyl or a group of the formula STR2 as well as corresponding hydroxy compounds of the formula STR3 wherein R6' is hydrogen, lower alkyl, a group of formula (a), (b), (c), (d) or (e) or a group of the formula exhibit mucosa-protective and/or gastric acid secretion-inhibiting properties, such that they can be used for the control or prevention of illnesses of the gastrointestinal tract, especially against gastric ulcers and/or duodenal ulcers.