99648-41-6

Upstream product

• 36913-91-4 nonaflyl anhydride 
• 18627-14-0 p-methoxybenzoyl(p-methoxyphenyl)diazomethane 
• 100-07-2 4-methoxy-benzoyl chloride 
• 120-44-5 1,4-di(4-methoxyphenyl)ethanone 
• 488-93-7 3-Furoic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 32460-09-6 2,3,4,5-tetrabromofuran 
• 5720-07-0 4-methoxyphenylboronic acid 
• 119-52-8 4,4'-dimethoxybenzoin 
• 67-56-1 methanol 
• 2132-62-9 4,4'-dimethoxydiphenylacetylene 
• 27895-95-0 2-bromo-1,2-bis(4-methoxyphenyl)ethanone 
• 103326-23-4 1,2,3,4-tetrakis-(4-methoxy-phenyl)-butane-1,4-dione 

Relevant academic research and scientific papers

Reaction control in heterogeneous catalysis using montmorillonite: Switching between acid-catalysed and red-ox processes

The use of montmorillonite, modified with a super-acid (CF3SO3H), in the presence of hydroquinone as a radical scavenger and under a nitrogen atmosphere, induced the formation of tetrasubstituted furans as the major product from benzoins. In the absence of a radical scavenger, the only products obtained were 1,2-diketones.

A facile and practical process for the synthesis of polysubstituted furans from alkynes using atmospheric oxygen as a terminal oxidant

We present here a facile and practical procedure for the synthesis of tetrasubstituted furans from alkynes catalyzed by palladium acetate together with cupric acetate in acetic acid, using atmospheric oxygen as a terminal oxidant. Various internal aromati

Synthesis of cyclopentadienyl alkyl ethers via Pd-catalyzed cyclotrimerization of diarylacetylenes

A novel efficient tandem cyclization-methoxylation reaction has been developed to synthesize cyclopentadienyl alkyl ethers via palladium-catalyzed trimerization of diarylethynes and elimination of one dimethoxymethyl benzene molecule. The reaction mechanism was investigated by the Q-Tof APCI-HRMS technique, and the fluorescent properties of the obtained compounds were studied in the solid state and in solution.

Unexpected base-promoted synthesis of tetrasubstituted furans via palladium-catalyzed oxidation and cyclization of carbon-carbon triple bond with molecular oxygen

A new approach to the synthesis of tetrasubstituted furans using aromatic alkynes catalyzed by PdClin DMA (N,N-dimethylacetamide)-H with dioxygen as the sole oxidant is described, in which the oxygen atom of the furan was from water. The preliminary mechanistic understanding of this transformation was investigated. Georg Thieme Verlag Stuttgart · New York.

Palladium-catalyzed oxidation and cyclization of carbon-carbon triple bonds in fluorous media using molecular oxygen

An intriguing, facile, and efficient oxidation and cyclization of alkynes catalyzed by Pd(OAc)2 in a fluorous biphasic system of N,N-dimethylacetamide (DMA) and perfluorodecalin directly with molecular oxygen is described, which opens an efficient access to tetrasubstituted furans. Under the optimized conditions, intermolecular reaction between diverse alkynes provides the corresponding mixture of regioisomers with appreciable selectivity. Intramolecular oxidation and cyclization of alkynes are also successfully demonstrated. The reaction proceeds efficiently under mild conditions with atmospheric oxygen as the sole oxidant. Georg Thieme Verlag Stuttgart · New York.

Site-selective Suzuki-Miyaura cross-coupling reactions of 2,3,4,5-tetrabromofuran

Suzuki-Miyaura reactions of 2,3,4,5-tetrabromofuran allow a convenient and site-selective synthesis of mono-, di- and tetraarylfurans which are not readily available by other methods.

Synthesis of tetrasubstituted furans via sequential Pd(OAc) 2/Zn(OTf)2-catalyzed oxidation and cydization of aromatic alkynes with molecular oxygen

The development of a new method for the synthesis of tetrasubstituted furans using aromatic alkynes is reported. The strategy involves a tandem process of palladium-catalyzed oxidation and Zn(OTf)2-catalyzed cyclization in the presence of molecular oxygen.

Palladium-catalyzed perarylation of 3-thiophene- and 3-furancarboxylic acids accompanied by C-H bond cleavage and decarboxylation

3-Thiophene- and 3-furancarboxylic acids efficiently undergo perarylation accompanied by cleavage of the three C-H bonds and decarboxylation upon treatment with excess aryl bromides in the presence of a palladium catalyst to give the corresponding tetraarylated products in good yields.

Sm/TiCl4 system induced reductive coupling reactions: Synthesis of tetraarylfurans

Induced by low valent titanium, tetraarylfurans have been synthesized in good yields starting from aroyl chlorides under mild and neutral conditions.

Synthesis and biological evaluation of a novel series of furans: Ligands selective for estrogen receptor α

A variety of nonsteroidal systems can function as ligands for the estrogen receptor (ER), in some cases showing selectivity for one of the two ER subtypes, ERα or ERβ. We have prepared a series of heterocycle-based (furans, thiophenes, and pyrroles) ligands for the estrogen receptor and assessed their behavior as ER ligands. An aldehyde enone conjugate addition approach and an enolate alkylation approach were developed to prepare the 1,4-dione systems that were precursors to the trisubstituted and tetrasubstituted systems, respectively. All of the diones were easily converted into the corresponding furans, but formation of the thiophenes and pyrroles from the more highly substituted 1,4-diones was problematical. Of the systems investigated, the tetrasubstituted furans proved to be most interesting. They were ERα bindingand potency-selective agents, with the triphenolic 3-alkyl-2,4,5-tris(4-hydroxyphenyl)furans (15a-d) displaying generally higher subtype binding selectivity than the bisphenolic analogues (15f-i). Binding selectivity for ERα was as high as 50-70-fold, and transcriptional activation studies showed that several members of this series were ERα selective agonists, with the best compound [3-ethyl-2,4,5-tris(4-hydroxyphenyl)furan, 15b] having full transcriptional activity on ERα while being inactive on ERβ. Comparative binding affinity analysis and molecular modeling were used to investigate the preferred binding mode adopted by the furan ligands, which appears to have the C(2) phenol mimicking the important role of the A-ring of estradiol. These ligands should be useful in studying the biological roles of both ERα and ERβ, and they might form the basis for the development of novel estrogen pharmaceuticals.