51483-92-2

Usage

InChI:InChI=1/C9H5BrO2/c10-6-1-2-9-7(5-6)8(11)3-4-12-9/h1-5H

Upstream product

• 52817-12-6 6-bromo-4-oxo-4H-chromene-3-carbaldehyde 
• 49660-57-3 6-bromochroman-4-one 
• 1450-75-5 5-Bromo-2-hydroxyacetophenone 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 109-94-4 formic acid ethyl ester 
• 118449-57-3 3-(4-bromophenoxy)propionitrile 
• 93670-18-9 3-(4-bromophenyloxy)-propionic acid 
• 106-41-2 4-bromo-phenol 
• 51085-91-7 6-bromo-4-oxo-4H-chromene-3-carboxylic acid 
• 115237-38-2 C₁₁H₁₂BrNO₂ 

Downstream Products

• 1277188-80-3 (2S,4R)-6-bromo-3,4-dihydro-2,4-diphenyl-2H-1-benzopyran-4-ol 
• 1260485-39-9 (E)-6-styrylchromone 
• 1354628-08-2 7-(5-bromo-2-hydroxyphenyl)-2-mercaptopyrido[2,3-d]pyrimidin-4-ol 
• 1354628-12-8 4-bromo-2-(2-(piperidin-1-yl)thiazolo[4,5-b]pyridin-5-yl)phenol 
• 1354628-39-9 4-bromo-2-(3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-6-yl)phenol 
• 1354627-95-4 5-(5-bromo-2-hydroxyphenyl)-1-methyl-3-phenyl-1H-imidazo[4,5-b]pyridine-2(3H)-thione 
• 1384433-44-6 2-(6-bromo-4-oxo-4H-chromen-3-yl)cyclohexa-2,5-diene-1,4-dione 
• 1218-80-0 6-bromoflavone 
• 1220531-63-4 6-bromo-2-phenylchroman-4-one 
• 1446428-45-0 6-(2-phenylethynyl)chromone 
• 1012781-44-0 6-bromo-2-cyclohexyl-4H-chromen-4-one 
• 38445-24-8 6-hydroxy-4H-1-benzopyran-4-one 
• 6665-83-4 6-hydroxyflavone 

Relevant academic research and scientific papers

Asymmetric Synthesis of Sakuranetin-Relevant Flavanones for the Identification of New Chiral Antifungal Leads

Discovery and efficient synthesis of new promising leads have a central role in agrochemical science. Reported herein is the sakuranetin-directed synergistic exploration of an asymmetric synthesis and an antifungal evaluation of chiral flavanones. A new palladium catalytic system with CarOx-type ligands was successfully identified for the highly enantioselective addition of arylboronic acids to chromones. This enabled the facile and programmable construction of a constellation of chiral flavanones (up to 98% yield and 97% ee), in which (R)-pinostrobin was efficiently constructed without laborious protecting/deprotecting operations. Its good performance in asymmetric induction and functional tolerance expanded the chemical space of pharmaceutically important flavanones. The chiral differentiation of flavanones based on antifungal activity and a concise structure-activity relationship model was disclosed and summarized. This synergistic project culminated with acquisition of the naturally unprecedented flavanones with better antifungal potentials than sakuranetin, in which the R-enantiomer of flavanone 54 (EC50 = 0.8 μM) demonstrated better performance than boscalid against Rhizoctonia solani. The novel scaffold and predicted new target compared with the commercial fungicides in the FRAC reinforce the value of further exploration.

NHC-catalyzed enantioselective C2-functionalization of 3-hydroxychromenonesviaα,β-unsaturated acyl azoliums

A novel synthetic method for enantioselective C2-functionalization of 3-hydroxychromenones promoted by N-heterocyclic carbenesviathe formation of α,β-unsaturated acyl azolium intermediates, which occurs with Coates-Claisen rearrangement is established. This synthetic strategy enabled the rapid assembly of enantiomerically enriched δ-hydroxychromenone-derived esters/amides under mild conditions with good to excellent yields and broad substrate scope.

Substituent-Oriented Synthesis of Substituted Pyrazoles/Chromeno[3,2- c]pyrazoles via Sequential Reactions of Chromones/3-Chlorochromones and Tosylhydrazones

A facile and efficient synthetic strategy for the chemoselective synthesis of monocyclic/tricyclic-fused pyrazoles was developed, and it was oriented by different 3-position substituents (H or Cl) on the chromones. The reaction proceeded in a one-pot sequential way with a broad substrate scope and moderate to excellent yields.

An Efficient Microwave-Assisted Propylphosphonic Anhydride (T3P )-Mediated One-Pot Chromone Synthesis via Enaminones

An efficient synthesis of 4 H -chromene-4-ones via enamino ketones, with cyclization by using T3P under microwave heating is described. This is the first report for the synthesis of chromones by using T3P . Significant features of this method include short reaction times and high-purity products.

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.

Silanediol-Catalyzed Chromenone Functionalization

Promising levels of enantiocontrol are observed in the silanediol-catalyzed addition of silyl ketene acetals to benzopyrylium triflates. This rare example of enantioselective, intermolecular chromenone functionalization with carbonyl-containing nucleophiles has potential applications in the synthesis of bioactive chromanones and tetrahydroxanthones.

2,3-Unsubstituted chromones and their enaminone precursors as versatile reagents for the synthesis of fused pyridines

A divergent and regioselective approach to fused pyridines was developed through formal [3 + 3] cyclocondensations from simple 2,3-unsubstituted chromones or their enaminone precursors.

Efficient synthesis of chromones with alkenyl functionalities by the heck reaction

The usefulness of the Heck reaction in the field of chromones has been demonstrated. Bromochromones with the halogen atom in their rings A and B were reacted with various terminal alkenes to give hitherto unknown alkenyl-substituted chromones. Reactivity of the substrates was found to markedly depend on the position of the bromine atom. Under phosphine-free conditions using a phase-transfer catalyst additive (tetrabutylammonium bromide), shorter reaction periods and usually higher yields were obtained.

Benzopyrans: Part 34 - Reactions of 3-substituted 1-benzopyran-4-ones with N-phenacylpyridinium bromide

N-Phenacylpyridinium bromide in the presence of potassium carbonate gives the indolizine 10 and pyridinium salt 12 with the aldehyde 1 as well as the acid 2, azirine 14 with the nitrile 3, and zwitterion 16 with the ester 4. The pyridinium bromide 12 is converted into 10, and a mixture of 5 and 10 on refluxing in pyridine and dimethylformamide, respectively.