150107-86-1

Upstream product

• 767303-58-2 1-(2-methoxyphenyl)-3-(4-methoxyphenyl)prop-2-yn-1-one 
• 3989-14-8 (4-methoxyphenylethynyl)trimethylsilane 
• 3327-24-0 1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one 
• 768-60-5 4-methoxyphenylacetylen 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 4143-74-2 4'-methoxyflavone 

Downstream Products

• 4143-74-2 4'-methoxyflavone 

Relevant academic research and scientific papers

One-pot synthesis of 3-haloflavones from flavones using Oxone and potassium halide as a halogenation reagent

A two-step, one-pot method has been developed for the synthesis of 3-haloflavones from the corresponding flavones. The method uses Oxone and potassium halide to produce the active molecular halogen in situ. The solvent (methanol) then participates in the reaction to afford the 2-methoxy-3-haloflavanone derivative. After adding sodium hydroxide, the corresponding 3-haloflavone product is obtained in good to excellent yields. This method provides a convenient synthesis of 3-chloro, 3-bromo and 3-iodo flavones from the same flavone starting material.

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.

Iodine-mediated direct synthesis of 3-iodoflavones

Molecular iodine has been used for the regioselective, one pot, direct synthesis of 3-iodoflavones from 2′-allyloxy chalcones, 2′-hydroxy chalcones and flavones. Allyl deprotection, cyclization dehydrogenation and α-iodination of 2′-allyloxychalcones has been achieved in a single step to offer 3-iodoflavones.

Photo-induced tandem cyclization of 3-iodoflavones with electron rich five-membered heteroarenes

Vinyl radicals were generated from 3-iodoflavones under a mercury lamp and tandem cyclization reactions occurred with five-membered heteroarenes entailing two consecutive C-C bond formations to synthesize benzo[e]chromeno[2,3-g]indol-13(1H)-one derivatives. The tandem cyclization reactions worked in acetonitrile without any additives such as transition metals, ligands and oxidants, giving rise to a broad variety of novel polycyclic xanthone frameworks in good yield under mild and environmentally friendly reaction conditions.

Synthesis and antifungal activities of natural and synthetic biflavonoids

The synthesis of some natural and synthetic biflavonoids was performed in good overall yields starting from readily available materials via high yielding aldol and Ullmann condensations. Some of these compounds, especially bichalcones, display an interesting activity against fungi, higher than that of the corresponding monomers.

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-iodo derivatives of flavones, thioflavones and thiochromones

The title compounds, 2-aryl-3-iodo-4H-1-benzopyrans and 2-alkyl or 2-aryl-3-iodo-4H-1-benzothiopyrans, were prepared by reaction of the corresponding heterocyclic derivatives with the iodine-cerium(IV) ammonium nitrate system under mild conditions. The scope and proposed mechanism of the reaction were also demonstrated.