18068-82-1

Usage

Uses

Used in Pharmaceutical Development:
2-Phenylfuro[3,2-b]pyridine is used as a key intermediate in the synthesis of various pharmaceutical compounds for its potential biological activities and pharmacological properties. Its unique structure allows for the development of new therapeutic agents that can target specific biological pathways or receptors.
Used in Materials Science:
In the field of materials science, 2-Phenylfuro[3,2-b]pyridine is utilized for its potential applications in the creation of new materials with specific properties. Its aromatic nature and heterocyclic structure contribute to the design and synthesis of materials with tailored characteristics for various applications.
Used in Organic Chemistry Research:
2-Phenylfuro[3,2-b]pyridine serves as an interesting target for research in organic chemistry due to its unique molecular structure and potential for further functionalization. It can be used to study reaction mechanisms, explore new synthetic routes, and develop novel compounds with desired properties.
Used in Drug Discovery:
As a promising candidate in drug discovery, 2-Phenylfuro[3,2-b]pyridine is employed for its potential to be developed into new drugs with therapeutic benefits. Its unique structure and properties make it a valuable starting point for the design and optimization of new pharmaceutical agents targeting various diseases and conditions.

Upstream product

• 13146-23-1 copper(I) phenylacetylenide 
• 40263-57-8 2-iodo-3-hydroxypyridine 
• 536-74-3 phenylacetylene 
• 6602-32-0 2-bromo-pyridin-3-ol 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 6636-78-8 2-chloro-3-hydroxypyridine 
• 100-52-7 benzaldehyde 
• 754131-60-7 3-bromo-2-(bromomethyl)pyridine 
• 52378-64-0 3-bromo-2-hydroxymethyl-pyridine 
• 30683-23-9 3-bromopicolinic acid 
• 23003-22-7 2-mercapto-3-pyridinol 
• 108-86-1 bromobenzene 
• 113503-65-4 2-bromo-3-isopropoxypyridine 
• 92671-70-0 acetic acid 2-bromopyridin-3-yl ester 

Relevant academic research and scientific papers

Copper- And ligand-free heteroannulation of o-halohydroxypyridine with terminal alkynes using Pd/C catalyst: One-pot synthesis of 2-substituted furopyridines and their functionalization

Three types of isomeric 2-substituted furo[3,2-b]pyridine, furo[2,3-b]pyridine and furo[3,2-c]pyridine were prepared using Pd/C-catalyzed heteroannulation of o-halopyridinols and terminal alkynes under copperand ligand-free conditions. We also demonstrated that double functionalization yielding 2,3-disubstituted furopyridines could be achieved through heteroannulation followed by bromination and Suzuki/Heck reactions. In addition, the use of recoverable Pd/C in the absence of a cocatalyst and ligand can aid in the development of greener chemical processes.

One-pot Tandem Heck alkynylation/cyclization reactions catalyzed by Bis(Pyrrolyl)pyridine based palladium pincer complexes

Ligand assisted palladium catalyzed one-pot tandem Heck alkynylation/cyclization reactions for the synthesis of benzofurans was reported in this paper. Well-defined palladium-pincer complexes exhibited excellent catalytic activities for the one-pot tandem Heck alkynylation/cyclization reactions yielding benzofuran derivatives using 0.1 molpercent catalyst. All the catalytic reactions are performed in air. The effects of variables such as solvents, the temperature on the catalytic activity are also reported. High product conversion was obtained for differently substituted 2-iodophenol at 120 °C in 10 h.

CuI catalyzed domino coupling–cyclization of 2-iodo-phenols and 1-alkynes to the synthesis of 2-substituted benzo[b]furans/furo-pyridines

CuI/proline-catalyzed coupling reaction of 2-iodo-phenols with terminal alkynes and the following cyclization process is carried out successively in DMSO at 80 °C. Under this tandem process, 2-substituted benzo[b]furans/furo-pyridines were synthesized in good to excellent yields with a great diversity.

Synthesis of benzofurans from terminal alkynes and iodophenols catalyzed by recyclable palladium nanoparticles supported on N,O-dual doped hierarchical porous carbon under copper- and ligand-free conditions

We herein report that a stable and recyclable heterogeneous catalyst, consisting of Pd nanoparticles supported on N,O-dual doped hierarchical porous carbon derived from naturally available and renewable biomass-bamboo shoots, which allows for highly efficient one-pot tandem reaction of o-iodophenols with terminal alkynes to synthesize biologically active 2-benzofuran derivatives under copper- and ligand-free conditions. The catalyst performed superior catalytic performance compared with the analogous Pd/C and supported on other metal oxides under otherwise identical conditions. A broad set of aryl and alkyl terminal alkynes can be effectively coupled /cyclized with various o-iodophenols to afford their corresponding 2-benzofurans in good to high yields with good tolerance of multiple functional groups. Moreover, the catalyst showed good stability and could be reused several times without significant loss of activity.

Facile synthesis of 2-substituted benzo[: B] furans and indoles by copper-catalyzed intramolecular cyclization of 2-alkynyl phenols and tosylanilines

A catalytic amount of CuCl and Cs2CO3 was employed to synthesize a variety of 2-substituted benzo[b]furans and indoles by an intramolecular cyclization of 2-alkynyl phenols and tosylanilines. This protocol features mild conditions, h

Strategy for Overcoming Full Reversibility of Intermolecular Radical Addition to Aldehydes: Tandem C-H and C-O Bonds Cleaving Cyclization of (Phenoxymethyl)arenes with Carbonyls to Benzofurans

An intermolecular addition of carbon radicals enabled by a cascade radical coupling strategy is developed. It includes an intermolecular alkyl radical addition to a carbonyl group followed by an intramolecular alkoxy radical addition to haloarenes and produces substituted benzofurans in high yields. The radical nature of this reaction is explored by radical trapping experiments and EPR analysis. The mechanism is investigated by KIE experiments and control experiments. This method could provide rapid and practical access to the key intermediate of TAM-16, a safe and potent antibacterial agent for treating tuberculosis, and, therefore, is of great importance for organic synthesis and the pharmaceutical industry.

Synthesis of Benzofurans and Indoles from Terminal Alkynes and Iodoaromatics Catalyzed by Recyclable Palladium Nanoparticles Immobilized on Siliceous Mesocellular Foam

Herein, we report on the utilization of a heterogeneous catalyst, consisting of Pd nanoparticles supported on a siliceous mesocellular foam (Pd0-AmP-MCF), for the synthesis of heterocycles. Reaction of o-iodophenols and protected o-iodoanilines with acetylenes in the presence of a Pd nanocatalyst produced 2-substituted benzofurans and indoles, respectively. In general, the catalytic protocol afforded the desired products in good to excellent yields under mild reaction conditions without the addition of ligands. Moreover, the structure of the reported Pd nanocatalyst was further elucidated with extended X-ray absorption fine-structure spectroscopy, and it was proven that the catalyst could be recycled multiple times without significant loss of activity.

Chelation-assisted C-S activation/cascade heteroannulation of pyridine-2-thione derivatives in Pd-catalyzed cross-coupling reaction with alkynes

Ortho-chelation assistance was proved to be crucial for the success of the desulfitative Sonogashira cross-coupling reaction of thioamide-type pyridine derivatives and alkynes. Corresponding alkynylated products were obtained with moderate to excellent yields. Thanks to this reaction, furo[3,2-b]pyridine and 1H-pyrrolo[3,2-b]pyridine derivatives were synthesized through a one-pot cross-coupling reaction/heteroannulation sequence.

Tandem Sonogashira-Hagihara coupling/cycloisomerization reactions of ethynylboronic acid MIDA ester to afford 2-heterocyclic boronic acid MIDA esters: A concise route to benzofurans, indoles, furopyridines and pyrrolopyridines

A one-pot process that provides direct access to 2-heterocyclic MIDA (N-methyliminodiacetic acid) boronates has been developed. The reaction of 2-iodophenols or 2-iodoanilines with ethynylboronic acid MIDA ester readily afforded 2-substituted heterocyclic compounds. Amidine and phosphazene bases, especially TMG (1,1,3,3-tetramethylguanidine) assumed an important role in the tandem Sonogashira-Hagihara coupling/cycloisomerization reactions.

Copper pincer complexes as advantageous catalysts for the heteroannulation of ortho-halophenols and alkynes

A new, non-symmetrical copper(II) pincer complex catalyzes much more efficiently the formation of benzofuran by the reaction between ortho-iodophenols and alkynes. The lowest catalyst loadings are realized for this reaction, and bromo- and chlorophenols are heteroannulated for the first time. Strong evidence for hydrophenoxylation and intramolecular halogen atom-transfer steps catalyzed by this remarkably active, recyclable homogeneous catalyst is provided.