51924-83-5

Upstream product

• 1145-93-3 diethyl 4-methoxybenzylphosphonate 
• 72398-68-6 2-(1-methoxy-ethoxy)-benzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 90-02-8 salicylaldehyde 
• 3462-97-3 (4-methoxybenzyl)triphenylphosphonium bromide 
• 98-80-6 phenylboronic acid 
• 637-69-4 4-Methoxystyrene 
• 653-34-9 2,3,4,5,6-pentafluorostyrene 
• 5661-50-7 N-(phenoxy)acetamide 
• 64908-64-1 2-phenoxyisoindol-1,3-dione 
• 4846-21-3 O-phenylhydroxylamine 
• 105-13-5 4-Methoxybenzyl alcohol 
• 696-62-8 para-iodoanisole 
• 81787-62-4 o-((trimethylsilyl)ethynyl)phenol 

Downstream Products

• 19234-04-9 2-(p-methoxyphenyl)-benzo[b]furan 

Relevant academic research and scientific papers

Method for synthesizing o-alkenyl phenol derivative through ring opening of benzofuran under catalysis of nickel

The invention belongs to the technical field of organic synthesis, and discloses a method for synthesizing an o-alkenyl phenol derivative through ring opening of benzofuran under catalysis of nickel. The method comprises the following step: in a protective atmosphere and with an organic solvent as a reaction medium, subjecting a benzofuran compound to reacting with a silicon-hydrogen compound under the action of a nickel catalyst and a ligand or the action of the nickel catalyst, the ligand and an additive to obtain a product containing a silicon protecting group, namely the o-alkenyl phenol derivative containing the silicon protecting group; or removing the silicon-containing protecting group to obtain the o-alkenyl phenol derivative, namely the o-alkenyl phenol derivative containing the phenolic hydroxyl group. According to the method, nickel is used as a catalyst, a phosphine compound or N-heterocyclic carbene is used as a ligand, and the method has the advantages of high yield, wide substrate applicability and the like. In addition, the benzofuran compound is used as a raw material in the reaction, so the method has the advantages of cheap and easily available raw materials, simplicity and convenience in operation, mild reaction conditions, good functional group position compatibility and the like, and has very high practicability.

Hydroxyl Assisted, Photoredox/Cobalt Co-catalyzed Semi-Hydrogenation and Tandem Cyclization of o-Alkynylphenols for Access to 2,3-Dihydrobenzofurans

Herein, a hydroxyl assisted, photoredox/cobalt co-catalyzed semi-hydrogenation and tandem cyclization of o-alkynylphenols is developed towards direct assembly of 2,3-dihydrobenzofurans. Moderate to good yields were obtained for a range of sterically and electronically diverse 2-propynolphenols under mild conditions. Mechanistic studies demonstrated the inevitable role of the alcoholic hydroxyl group with (Z)-alkene as the real intermediate. Finally, a key low-valent cobalt catalyzed intramolecular hydroetherification of alkene is proposed. (Figure presented.).

Preparation method of benzofuran derivative

The invention belongs to the field of organic chemical synthesis, and particularly relates to a preparation method of a benzofuran derivative. According to the specific technical scheme, the preparation method of the benzofuran derivative comprises the fo

Late-Stage Direct o-Alkenylation of Phenols by PdII-Catalyzed C?H Functionalization

o-Alkenylation of unprotected phenols has been developed by direct C?H functionalization catalyzed by PdII. This work features phenol group as a directing group and realizes highly site-selective C?H bond functionalization of phenols to achieve the corresponding products in moderate to excellent yields at 60 °C. The advantages of this reaction include unprecedented C?H functionalization using phenol as a directing group, high regioselectivity, good substrate scope, mild reaction conditions, and high efficiency. To the best of our knowledge, this is the first example of a regioselective C?H alkenylation of unprotected phenols utilizing phenolic hydroxyl group as a directing group. The alkenylation of unprotected tyrosine and intramolecular cyclization are also successfully carried out under this catalytic system in good yields. Furthermore, this novel method enables a late-stage modification of complex phenol-containing bioactive molecules toward a diversity-oriented drug discovery.

HFIP Solvent Enables Alcohols to Act as Alkylating Agents in Stereoselective Heterocyclization

A new method for the stereoselective synthesis of highly functionalized oxygen heterocycles using allyl or benzyl alcohols as alkylating agents is presented. The process is efficient and atom economic, generating water as the only stoichiometric byproduct. Substoichiometric amounts of Ti(OiPr)4 in HFIP solvent are key to this reactivity, and the method tolerates a broad substitution pattern on both the alcohol initiator and homoallylic alcohol substrate. Preliminary mechanistic studies reveal in situ formation of a titanium complex with HFIP which may initiate the cyclization reaction. Further stereoselective functionalization of the products allows access to a diverse range of interesting heterocyclic structures.

Decarboxylation of α,β-unsaturated aromatic lactones: Synthesis of: E-ortho -hydroxystilbenes from 3-arylcoumarins or isoaurones

A simple and environmentally friendly strategy for the synthesis of E-ortho-hydroxystilbenes has been established. Two kinds of α,β-unsaturated aromatic lactones, i.e. the 3-arylcoumarins and the isoaurones, could both readily undergo a cascade hydrolyzation/decarboxylation reaction in the presence of KOH in ethylene glycol to afford the desired E-ortho-hydroxystilbenes in moderate to high yields.

Hypervalent Iodine(III)-Catalyzed Synthesis of 2-Arylbenzofurans

An alternative route for the synthesis of 2-arylbenzofurans is described by iodine(III)-catalyzed oxidative cyclization of 2-hydroxystilbenes using 10 mol% (diacetoxyiodo)benzene [PhI(OAc) 2 ] as catalyst in the presence of m -chloroperbenzoic acid. The 2-arylbenzofurans were isolated in good to excellent yields.

Diarylethenes display in vitro anti-TB activity and are efficient hits targeting the mycobacterium tuberculosis HU Protein

Tuberculosis continues to be a great source of concern in global health because of the large reservoir of humans infected with the bacilli and the appearance of clinical isolates resistant to a wide array of anti-tuberculosis drugs. New drugs with novel mechanisms of action on new targets are urgently required to reduce global tuberculosis burden. Mycobacterium tuberculosis nucleoid associated protein (NAP) HU has been shown to be druggable and essential for the organism’s survival. In this study, four diarylethenes were synthesized using a one-pot decarboxylated Heck-coupling of coumaric acids with iodoanisoles. The prepared compounds 1–4 were tested for their in vitro growth inhibition of M. tuberculosis H37Rv using the spot culture growth inhibition assay, displaying minimum inhibitory concentrations between 9 and 22 μM. Their cytotoxicity against BHK-21 cell line showed half inhibition at concentrations between 98 and 729 μM. The most selective hit (SI = 81), demonstrated inhibition of M. tuberculosis HU protein involved in maintaining bacterial genome architecture.

One-Step Synthesis of Substituted Benzofurans from ortho- Alkenylphenols via Palladium-Catalyzed C=H Functionalization

A dehydrogenative oxygenation of C(sp2)=H bonds with intramolecular phenolic hydroxy groups has been developed, which provides a straightforward and concise access to structurally diversely benzofurans from ortho-alkenylphenols. The reaction is catalyzed by palladium on carbon (Pd/C) without any oxidants and sacrificing hydrogen acceptors.

Inhibitory effect of cytotoxic stilbenes related to resveratrol on the expression of the VEGF, hTERT and c-Myc genes

A group of thirty-nine stilbene derivatives, prepared by means of Heck coupling reactions, has been investigated for their cytotoxicity, as well as for their ability to inhibit the production of the vascular endothelial growth factor (VEGF) and the activation of telomerase. The ability of these compounds to inhibit proliferation of two tumoral cell lines (HT-29 and MCF-7) and one non tumoral cell line (HEK-293) was first determined. Subsequently, we determined the capacity of the compounds to inhibit the secretion of VEGF in the aforementioned cell lines and to downregulate the expression of the VEGF, hTERT and c-Myc genes, the two latter involved in the control of the activation of telomerase. One of the synthetic stilbenes, (E)-4-(4-methoxystyryl)aniline, showed strong cytotoxicity and proved able to cause a marked decrease both in the secretion of VEGF and in the expression of the hTERT and c-Myc genes, in all cases at concentrations in the low nanomolar range.