40358-49-4

Upstream product

• 498-60-2 furan-3-carboxaldehyde 
• 108-86-1 bromobenzene 
• 591-51-5 phenyllithium 
• 117305-67-6 6-phenyl-2,7-dioxabicyclo[3.2.0]hept-3-ene 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 62495-31-2 3-(phenylmethyl)furan 
• 1016926-23-0 2-phenyl-furan-3-carboxaldehyde 
• 136131-55-0 2-benzyl-8-phenyl-1-naphthol 
• 136131-56-1 2-benzyl-8-carbomethoxy-1-naphthol 
• 136131-54-9 2-benzyl-8-methyl-1-naphthol 
• 136131-41-4 2-benzyl-1,4-dihydro-1,4-epoxynaphthalene 
• 123239-69-0 3-benzyl-1-naphthol 
• 36441-32-4 2-benzyl-1-naphthol 

Relevant academic research and scientific papers

Singlet-oxygen-induced rearrangement of furan derivatives

Upon exposure to singlet oxygen and dimethylsulfide, the addition products between 3-furaldehydes and Grignard reagents undergo an oxidative rearrangement to give 2-substituted 3-furaldehydes, in yields ranging from 26-83%. N-Aryl- and N-tosylpyrroles were similarly obtained if the corresponding nitrogen-containing precursors were used instead, in equally attractive yields (64-92%). Georg Thieme Verlag Stuttgart - New York.

Addition/oxidative rearrangement of 3-furfurals and 3-furyl imines: New approaches to substituted furans and pyrroles

Furans and pyrroles are important synthons in chemical synthesis and are commonly found in natural products, pharmaceutical agents, and materials. Introduced herein are three methods to prepare 2-substituted 3-furfurals starting from 3-furfural, 3-bromofuran, and 3-vinylfurans. Addition of a variety of organofithium, Grignard, and organozinc reagents (M-R) to 3-furfural provides 3-furyl alcohols in high yields. Treatment of these intermediates with NBS initiates a novel oxidative rearrangement that results in the installation of the R group in the 2 position of the 2-substituted 3-furfurals. Likewise, metalation of 3-bromofuran with n-BuLi and addition to benzaldehyde provides a furyl alcohol that is converted to 2-phenyl 3-furfural upon oxidative rearrangement. Enantioenriched disubstituted furans can be prepared starting with the Sharpless asymmetric dihydroxylation of 3-vinylfurans. The resulting enantioenriched diols undergo the oxidative rearrangement to furnish enantioenriched 2-substituted 3-furfurals with excellent transfer of asymmetry. This later method has been applied to the enantioselective preparation of an intermediate in Honda's synthesis of the natural product (-)-canadensolide. Mechanistic studies involving deuterium-labeled furyl alcohol suggest that the oxidative rearrangement proceeds through an unsaturated 1,4-dialdehyde intermediate. The alcohol then cyclizes onto an aldehyde, resulting in the elimination of water and rearomatization. On the basis of this proposed mechanism, we found that 3-furyl imines undergo the addition of organometallic reagents to provide furyl sulfonamides. Under the oxidative rearrangement conditions, 2-substituted 3-formyl pyrroles are formed, providing a novel route to these heterocycles. In contrast to the metalation of heterocycles, which often lead to mixtures of regioisomeric products, these new oxidative rearrangements of furyl alcohols and furyl sulfonamides generate only one regioisomer in each case.

Oxidation of 3-furfurylcarbinols with bromine in acetone-water

Oxidation of 3-furfurylcarbinols 3a-e and 7 with bromine in acetone-water solution gave the 2-substituted-3-furfurals 4a-e and 8 in good yields, respectively. Reaction of 2-alkyl-3-furfurylcarbinols 9a and 9b with bromine in acetone-water gave the bromoal

Design, synthesis, and structure-activity relationships of pyrazolo[3,4-d]pyrimidines: A novel class of potent enterovirus inhibitors

A series of pyrazolo[3,4-d]pyrimidines were synthesized and their antiviral activity was evaluated in a plaque reduction assay. It is very interesting that this class of compounds provide remarkable evidence that they are very specific for human enteroviruses, in particular, coxsackieviruses. Some derivatives proved to be highly effective in inhibiting enterovirus replication at nanomolar concentrations. SAR studies revealed that the phenyl group at the N-1 position and the hydrophobic diarylmethyl group at the piperazine largely influenced the in vitro antienteroviral activity of this new class of potent antiviral agents. It was found that the pyrazolo[3,4-d]pyrimidines with a thiophene substituent, such as compounds 20-24, in general exhibited high activity against coxsackievirus B3 (IC50=0.063-0.089μM) and moderate activity against enterovirus 71 (IC50=0.32-0.65μM) with no apparent cytotoxic effect toward RD (rhabdomyosarcoma) cell lines (CC5025μ M).

5,10,15-Triaryl-21,23-dioxacorrole and its isomer with a protruding furan ring

An oxa-analogue of 5,10,15-triarylcorrole, i.e., 5,10,15-triaryl-21,23-dioxacorrole (21,23-O2Cor)H, where two pyrrole rings are replaced by furan moieties, has been produced by condensation of 2,5-bis(arylhydroxymethyl)furan, 2-phenylhydroxymethylfuran, and pyrrole. 2-Phenylhydroxymethylfuran serves as the suitable synthone to introduce a furan ring with the ability create a direct pyrrole-furan α-α bond. The replacement of 2-phenylhydroxymethylfuran by 3-phenylhydroxymethylfuran led to a nonaromatic isomer of (21,23-O2Cor)H, i.e., (iso-21,23-O2Cor)H, which accommodates two furan rings. The protruding furan is built into the macrocycle via β and β′ carbon atoms with the oxygen atom pointing outward. Crystal structures of the [(21,23-O2Cor)H2]2[ZnCl4] and [(iso-21,23-O2Cor)H2] Cl have been studied by X-ray crystallography. The complex ZnCl42- anion is located in a clam-shell-like cavity formed by two 21,23-dioxacorrole cations of the [(21,23-O2-Cor)H2]2[ZnCl4] unit. The 21,23-dioxacorrole cation is only slightly distorted from planarity. In [(iso-21,23-O2Cor)H2]Cl, the macrocycle is strongly puckered as the internal ring is contracted by two carbon atoms when compared to regular porphyrin. The chloride anion is located over the center of the macrocycle and is involved in two intra (N)···HCl and two intermolecular (C)···HCl interactions to be classified as a tetrafurcate system. The (21,23-O2Cor)H molecule preserves aromaticity of the parental corrole with characteristic downfield positions of furan and pyrrole resonances in 1H NMR accompanied the NH resonance at the upfield position (-2.53 ppm). The temperature- dependent features detected in 1H NMR spectra of (21,23-O2Cor)H are consistent with the existence of a tautomeric equilibrium which involves two tautomers alternatively protonated on N(22) or N(24) nitrogen atoms. The density functional theory (DFT) has been applied to model the molecular and electronic structure of two tautomers of 21,23-dioxacorrole {22-N, 24-NH}, {22-NH, 24-N}. The total energies calculated using the B3LYP/6-31G**//B3LYP/6-31G* approach demonstrate a very small energy difference (1.4 kcal/mol) between tautomers suggesting their simultaneous presence in equilibrium. Insertion of nickel(II) into (21,23-O2Cor)H yields five-coordinate (21,23-O2Cor)NiIICl-the first high-spin nickel(II) in a corrole-like macrocyclic environment.

Benzylation via Tandem Grignard Reaction - Iodotrimethylsilane (TMSI) Mediated Reduction

A method has been developed which allows for the large scale preparation of biarylmethanes.This method involves the initial formation of biarylmethanols via reaction of aryl Grignards with carbonyl compounds followed by a subsequent reduction with iodotrimethylsilane (TMSI).A number of improvements over existing literature procedures are reported as well as previously unobserved dimerizations.Studies reveal that as few as 3 equiv of TMSI will give complete reduction in most cases where either of the substituents are not heteroaromatic.Mono-substituted alkanols react with TMSI to afford the corresponding iodides.A mechanistic study of the TMSI reduction is also reported.