767303-58-2

Upstream product

• 3989-14-8 (4-methoxyphenylethynyl)trimethylsilane 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 135-02-4 ortho-anisaldehyde 
• 768-60-5 4-methoxyphenylacetylen 
• 89-95-2 2-methyl-benzyl alcohol 
• 767303-68-4 3-(4-methoxy-phenyl)-1-(2-methoxy-phenyl)-prop-2-yn-1-ol 

Downstream Products

• 71993-33-4 3-chloro-2-(4-methoxyphenyl)-4H-chromen-4-one 
• 1332698-03-9 2-(4-methoxyphenyl)-3-(phenylselenyl)-4H-chromen-4-one 
• 150107-86-1 3-iodo-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one 

Relevant academic research and scientific papers

Heterocyclic Iodoniums for the Assembly of Oxygen-Bridged Polycyclic Heteroarenes with Water as the Oxygen Source

A diverse set of novel heterocyclic iodoniums was synthesized for the first time. The reactions of these unique iodoniums with environmentally benign water as the oxygen source provided structurally complex oxygen-incorporated heteropolycycles that are essential motifs in natural products and biologically active compounds. The transformation only required low-cost copper acetate. Further derivatization of the obtained polycycles expanded the structural diversity, which is important in the building of chemical libraries for drug discovery.

One-Pot Domino Friedel-Crafts Acylation/Annulation between Alkynes and 2-Methoxybenzoyl Chlorides: Synthesis of 2,3-Disubstituted Chromen-4-one Derivatives

A highly regioselective synthesis of 2,3-disubstituted chromen-4-one derivatives is accomplished from readily available internal alkynes and 2-methoxybenzoyl chlorides. The reaction proceeds via a domino intermolecular Friedel-Crafts acylation/intramolecular vinyl carbocation trapping (or oxa-Michael addition)/demethylation reaction sequence. This Lewis acid promoted method features relatively mild reaction conditions to synthesize a variety of 2,3-disubstituted chromen-4-one derivatives in one pot with up to 93% yield. The chromen-2-one (coumarin) product was obtained when 2,6-dimethoxybenzoyl chloride was used as a starting material via an electrophilic aromatic substitution/rearrangement process.

Divergence in Ynone Reactivity: Atypical Cyclization by 3,4-Difunctionalization versus Rare Bis(cyclization)

Functionalized ynones can be activated by Tf2C=CH2, which was generated in situ, to form zwitterionic species. These species were trapped in an intramolecular fashion by several nucleophiles to generate two major types of triflones in a divergent manner. Through fine-tuning of the reaction temperature, bis(triflyl)-6-membered- or (triflyl)-5-membered-fused-heterocycles were achieved in reasonable yields in a totally selective manner. In this way, bis(triflyl)flavones, bis(triflyl)thioflavones, bis(triflyl)selenoflavones, (triflyl)benzothienopyrans, (triflyl)benzoselenophenopyrans, (triflyl)vinyl aurones, and (triflyl)pyranoindoles were constructed. Conceivable mechanistic pathways were suggested on the basis of the isolation of several intermediates and the results from control experiments.

Palladium-, ligand-, and solvent-free synthesis of ynones by the coupling of acyl chlorides and terminal alkynes in the presence of a reusable copper nanoparticle catalyst

Supported copper nanoparticles are utilized for the first time as a highly efficient and reusable catalyst in the coupling of acyl chlorides and terminal alkynes to prepare various ynones. The reaction is carried out under palladium-, ligand-, and solvent

Copper-free Sonogashira coupling of acid chlorides with terminal alkynes in the presence of a reusable palladium catalyst: An improved synthesis of 3-iodochromenones (= 3-iodo-4H-1-benzopyran-4-ones)

Pd/C is used as an efficient catalyst for the copper-free Sonogashira coupling of acid chlorides and terminal alkynes to afford ynones in high yields (Tables 1 and 3). Cyclization of (2-methoxyaryl)-substituted ynones induced by I2/ammonium cer

Diversity-oriented synthesis of 3-iodochromones and heteroatom analogues via ICl-induced cyclization

The ICl-induced cyclization of heteroatom-substituted alkynones provides a simple, highly efficient approach to various 3-iodochromones and analogues. This process is run under mild conditions, tolerates various functional groups, and generally provides chromones in good to excellent yields. Subsequent palladium-catalyzed transformations afford a rapid increase in molecular complexity and a convenient preparation of a wide range of functionally substituted chromones, furans, and polycyclic compounds. Iodothiochromenones and iodoquinolinones are also prepared by similar ICl-induced cyclizations.

Synthesis of 3-halogenated flavonoids via electrophile-promoted cyclization of 2-(3-aryl-2-propynoyl)anisoles

Treatment of 2-(1-aryl-3-propynoyl) anisoles 1 with N-chlorosuccinimide (NCS) or N-bromosuccinimide (NBS) gave the 3-halogenated flavones and their related molecules in moderate yields.