130252-74-3

Upstream product

• 123743-15-7 6-chloro-2-(4-methoxyphenyl)chroman-4-one 
• 73220-32-3 (2E)-1-(5-chloro-2-hydroxyphenyl)-3-(dimethylamino)-2-propen-1-one 
• 68-12-2 N,N-dimethyl-formamide 
• 3438-16-2 5-chloro-2-methoxybenzoic acid 
• 70744-47-7 (p-methoxyphenyl)tri-n-butylstannane 
• 73220-38-9 3-bromo-6-chloro-4H-1-benzopyran-4-one 
• 73220-39-0 6-chloro-3-iodo-4H-chromen-4-one 
• 5720-07-0 4-methoxyphenylboronic acid 
• 1450-74-4 5-chloro-2-hydroxyacetophenone 
• 33397-21-6 tris(4-methoxyphenyl)bismuth 

Relevant academic research and scientific papers

Stille coupling for the synthesis of isoflavones by a reusable palladium catalyst in water

Isoflavones were synthesized from the reaction of 3-bromochromone derivatives and aryltributylstannanes via Stille coupling catalyzed by a water-soluble and reusable PdCl2(NH3)2/2,2′-cationic bipyridyl system in aqueous solution. For prototype 3-bromochromone, the coupling reaction was performed at 80°C for 24 hr with 2.5 mol% catalyst in water in the presence of tetrabutylammonium fluoride. After the reaction, the aqueous solution could be reused for several runs, indicating that its activity was only slightly decreased. For substituted 3-bromochromones, the addition of NaHCO3 and a higher reaction temperature (120°C) were required to gain satisfactory outcomes. In addition, naturally occurring products, such as daidzein, could be obtained by this protocol via a one-pot reaction.

Synthesis, antimycobacterial evaluation and pharmacophore modeling of analogues of the natural product formononetin

Abstract The synthesis and antimycobacterial activity of formononetin analogues is hereby reported. Formononetin and its analogue 11E showed 88% and 95% growth inhibition, respectively, against the H37Rv strain of Mycobacterium tuberculosis. Pharmacophore modeling studies indicated that the presence of a hydroxyl group in formononetin and its analogues, is crucial for maintaining activity.

Pd-Catalyzed efficient cross-couplings of 3-iodochromones with triarylbismuths as substoichiometric multicoupling organometallic nucleophiles

An efficient cross-coupling of 3-iodochromones with triarylbismuths under catalytic palladium conditions is reported. Triarylbismuths were employed as substoichiometric multicoupling nucleophiles for the synthesis of a variety of substituted isoflavones.

Hypervalent Iodine Oxidation of Flawanones: Convenient and Useful Syntheses of Flavones and IsoFlavones

Hypervalent iodine oxidation of flavanones (1a-g) under a variety of conditions, offering convenient and valuable routes to the syntheses of flavones (2a-g) and isoflavones (3a-g), is described.The course of these oxidation reactions is greatly influenced by the reaction conditions and it is possible to select appropriate conditions for following a desired route (2/3).The mechanistic rationale for these transformations is also discussed.

Hypervalent iodine oxidation of flavanones: A new synthesis of methyl 2-aryl-2,3-dihydrobenzofuran-3-carboxylates by 1,2-aryl shift

Flavanones (1), on oxidation with (diacetoxyiodo)benzene-sulfuric acid (DIB-H2SO4) or (hydroxy(tosyloxy)iodo)benzene (HTIB) in trimethyl orthoformate, undergo facile ring contraction by 1,2-aryl shift, thereby yielding methyl 2-aryl-2,3-dihydrobenzofuran-3-carboxylates (4) as major products (40-80%). cis-3-Methoxyflavanones (5) and flavones (3) are the minor products formed in variable ratios.

Oxidation of Flavanones using Thallium(III) Salts: A New Route for the Synthesis of Flavones and Isoflavones

When treated with thallium(III) acetate in acetic acid or acetonitrile, flavanones undergo facile dehydrogenation to afford flavones whereas, upon treatment with thallium(III) toluene-p-sulfonate or thallium(III) nitrate in propionitrile or acetonitrile, respectively, they undergo oxidative 2,3-aryl migration to give isoflavones in high yield.

Oxidative 1,2-aryl rearrangement in flavanones using thallium(III) p-tolylsulphonate (TTS): A new useful route to isoflavones

Oxidation of flavanones using thallium(III) p-tolylsulphonate (prepared in situ by the reaction of thallium(III) acetate and p-toluene sulphonic acid) in propionitrile leads to 1,2-aryl shift providing a new useful route to the synthesis of isoflavones.