58113-12-5

Upstream product

• 49619-82-1 3-bromo-4H-chromen-4-one 
• 5720-05-8 4-methylphenylboronic acid 
• 89839-87-2 2-(4-methylphenyl)-2,3-dihydro-4H-chromen-4-one 
• 122775-34-2 3-iodo-chromen-4-one 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 31614-66-1 tributyl(p-tolyl)stannane 
• 106129-86-6 1-(2-hydroxyphenyl)-3-dimethylaminoprop-2-enone 
• 1776-08-5 (E)-3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 5142-75-6 tri(p-tolyl)bismuth 
• 13400-26-5 3-hydroxychromen-4-one 
• 491-38-3 1-benzopyran-4(4H)-one 
• 118-93-4 o-hydroxyacetophenone 
• 1258792-31-2 3-(2-bromophenyl)-2-(4-methylphenyl)-3-oxopropanal 
• 220503-15-1 C₁₅H₁₃BrO 

Downstream Products

• 42327-60-6 4’-methylisoflavanone 
• 1606136-83-7 2-methyl-6-(4-methylphenyl)-7-(2-hydroxylphenyl)pyrazolo[1,5-a]pyrimidine 
• 1456626-69-9 3-cyano-6-(2-hydroxyphenyl)-5-(4-methylphenyl)pyridin-2(1H)-one 
• 1427272-76-1 3-cyano-6-(2-hydroxylphenyl)-5-(4-methylphenyl)pyridine-2-(1H)-thione 

Relevant academic research and scientific papers

Novel Synthesis of Isoflavones by the Palladium-Catalyzed Cross-Coupling Reaction of 3-Bromochromones with Arylboronic Acids or Its Esters

The synthesis of isoflavone derivatives by means of palladium-catalyzed cross-coupling reaction between 3-bromochromones and arylboronic acids or its butyl esters is described.

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.

Transient and Recyclable Halogenation Coupling (TRHC) for Isoflavonoid Synthesis with Site-Selective Arylation

A transient and recyclable C?H iodination has been designed for the synthesis of isoflavonoids through the domino reactions of o-hydroxyphenyl enaminones and aryl boronic acids in the presence of catalytic KI and Pd catalyst. Instead of the conventional cross-coupling strategy employing pre-halogenated substrates, this method transforms raw C?H bond by means of a transient C?H halogenation to smoothly relay the subsequent C-arylation. Consequently, such a method avoids the pre-functionalization for C?halogen bond installation as well as the generation of stoichiometric halogen-containing waste following the cross-coupled product, disclosing an intriguing new coupling protocol to forge the C?C bond in the virgin area between classical C?X (X=halogen) bond cross coupling and the C?H activation.

Pot-economic synthesis of diarylpyrazoles and pyrimidines involving Pd-catalyzed cross-coupling of 3-trifloxychromone and triarylbismuth

Abstract: The present study reveals the formation of 3,4-diarylpyrazole and 4,5-diarylpyrimidine in one-pot operation starting from 3-trifloxychromone and triarylbismuth. The complete process encompasses two steps in the one-pot operation. The first step leads to the formation of isoflavone via cross-coupling reaction of 3-trifloxychromone and triarylbismuth as a threefold arylating reagent. These isoflavones were further converted into 3,4-diarylpyrazole and 4,5-diarylpyrimidine using hydrazine hydrate and guanidinium chloride in the successive step in the same pot. Interestingly the formation of 3,4-diarylpyrazole was achieved in the shortest reaction time i.e., 30 min that too at room temperature. Overall the developed methodology provides easy access to the medicinally important diarylpyrazole and pyrimidine moiety in one-pot operation and in short reaction time. Graphical Abstract: Synopsis The work presented here describes the novel methodology for the formation of medicinally important heterocycles 3,4-diarylpyrazole and 4,5-diarylpyrimidine in one-pot operation starting from 3-trifloxychromone and triarylbismuth.

Scaffold-hopping of bioactive flavonoids: Discovery of aryl-pyridopyrimidinones as potent anticancer agents that inhibit catalytic role of topoisomerase IIα

A strategy of scaffold-hopping of bioactive natural products, flavones and isoflavones, leading to target-based discovery of potent anticancer agents has been reported for the first time. Scaffold-hopped flavones, 2-aryl-4H-pyrido[1,2-a]pyrimidin-4-ones and the scaffold-hopped isoflavones, 3-aryl-pyrido[1,2-a]pyrimidin-4-ones were synthesized via Pd-catalyzed activation–arylation methods. Most of the compounds were found to exhibit pronounced human topoisomerase IIα (hTopoIIα) inhibitory activities and several compounds were found to be more potent than etoposide (a hTopoIIα-inhibiting anticancer drug). These classes of compounds were found to be hTopoIIα-selective catalytic inhibitors while not interfering with topoisomerase I and interacted with DNA plausibly in groove domain. Cytotoxicities against various cancer cells, low toxicity in normal cells, and apoptotic effects were observed. Interestingly, compared to parent flavones/isoflavones, their scaffold-hopped analogs bearing alike functionalities showed significant/enhanced hTopoIIα-inhibitory and cytotoxic properties, indicating the importance of a natural product-based scaffold-hopping strategy in the drug discovery.

A novel synthesis of isoflavones via copper(I)-catalyzed intramolecular cyclization reaction

Isoflavone derivatives were synthesized via intramolecular cyclization of 3-(2-bromophenyl)-3-oxopropanal derivatives, using CuI as the catalyst, 2-picolinic acid (=pyridine-2-carboxylic acid) as the ligand, K 2CO3 as the base, and DMF as the solvent, in up to 96% yield. The synthesis is functional group-tolerant. Copyright

Oxidative rearrangements of 2'-hydroxychalcones with lh-l-hydroxy-5-methyl- l,2,3-benziodoxathiole 3,3-dioxide

1H-l-hydroxy-5-methyl-l,2,3-benziodoxathiole 3,3-dioxide (HMBI) has been found to effect the direct conversion of 2'-hydroxychalcones with various B-ring substituents to isoflavones in moderate to good yield (34-83%) in methanol under reflux. The reduced byproduct of HMBI is easily recovered by aqueous extraction and can be recycled and reused with high efficiency. Previous reports of conversions of this type required the use of toxic thallium(III) salts or initial protection of the 2'-hydroxyl group.

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.

Rapid syntheses of (±)-pterocarpans and isoflavones via the gold-catalyzed annulation of aldehydes and alkynes

(±)-Pterocarpan and analogues (4a-c) have been synthesized efficiently via the annulation of salicylaldehydes (1a, 1b and 1c) and o-methoxymethoxylphenylacetylene (2a), followed by a one-pot reduction and acidic cyclization of the ketones (3a-c). In addition, isoflavone derivatives (5a-c) have been synthesized rapidly, in two steps, via the annulation of salicylaldehyde (1a) and arylacetylenes (2b, 2c and 2d), followed by IBX/DMSO oxidation of the isoflavanones (3d, 3e and 3f).

A general method for the synthesis of isoflavones by oxidative rearrangement of flavanones using thallium (III) perchlorate

Oxidation of flavanones with thallium(III) perchlorate in acetonitrile or dimethoxyethane leads to 2,3-aryl migration providing a general method for the synthesis of isoflavones having electron relasing as well as electron withdrawing substituents at C2-aryl ring and the mechanism in relaltion to in vivo is discussed.