1786-05-6

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 16, p. 407, 1951 DOI: 10.1021/jo01143a009

InChI:InChI=1/C15H10O3/c16-14-11-8-4-5-9-12(11)18-15(17)13(14)10-6-2-1-3-7-10/h1-9,17H

Upstream product

• 83-13-6 diethyl 2-phenylmalonate 
• 108-95-2 phenol 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 3076-54-8 phenyllead(IV) triacetate 
• 507233-69-4 triphenyl bismuth ⁽²⁺⁾; dichloride 
• 28899-97-0 triphenylbismuth(V) diacetate 
• 28719-52-0 triphenylbismuth dinitrate 
• 93012-49-8 2-(phenylacetoxy)benzoic acid methyl ester 
• 103-82-2 phenylacetic acid 
• 118-55-8 phenyl Salicylate 
• 722-01-0 phenyl phenylacetate 
• 103-80-0 phenylacetyl chloride 
• 119-36-8 methyl salicylate 
• 86795-49-5 3-(phenyl-λ³-iodanylidene)chromane-2,4-dione 

Downstream Products

• 2288-98-4 <2>benzopyrano<4,3-c><1>benzopyran-5,12-dione 
• 78859-81-1 4-Benzoyloxy-3-phenyl-2H-benzopyran-2-on 
• 96600-93-0 3-(2-Hydroxyphenyl)-2-phenyl-1-thiomethylpropan-3-one 
• 96600-94-1 6H-<2>Benzopyrano<4,3-c><1>benzopyran-11-one 
• 91622-61-6 4-Phenylamino-3-phenyl-<1>benzopyran-2-on 
• 114832-90-5 3-phenyl-4-(phenylacetoxy)-coumarin 
• 1447565-24-3 2',3'-diphenylspiro[chroman-3,1'-indene]-2,4-dione 
• 1447565-43-6 3,5,6-triphenyl-2H-pyrano[2,3,4-de]chromen-2-one 
• 2491-31-8 2-hydroxy-deoxybenzoin 
• 1399134-34-9 4-(benzyloxy)-3-phenylcoumarin 
• 64555-47-1 4-[(1'-Methyl-2'-piperidinyl)-methoxy]-3-phenyl-coumarin 
• 64556-38-3 4-(3'-Piperidino-2'-methylpropoxy)-3-phenyl-coumarin 
• 64555-50-6 4-(2-methyl-3-morpholin-4-yl-propoxy)-3-phenyl-chromen-2-one 
• 64555-45-9 4-(3-morpholin-4-yl-propoxy)-3-phenyl-chromen-2-one 

Relevant academic research and scientific papers

Regioselective Chlorination and Suzuki–Miyaura Cross-Coupling of 4-Alkoxycoumarins, 4-Alkoxy-2-pyrones, and Related Heterocycles

Chlorination of the coumarin framework was achieved by using trichloroisocyanuric acid, which has several advantages over N-chlorosuccinimide, particularly with respect to cost-effectiveness and toxicity. The Suzuki–Miyaura cross-coupling of the chlorinat

Coumestan inhibits radical-induced oxidation of DNA: Is hydroxyl a necessary functional group?

Coumestan is a natural tetracycle with a C - C bond shared by a coumarin moiety and a benzofuran moiety. In addition to the function of the hydroxyl group on the antioxidant activity of coumestan, it is worth exploring the influence of the oxygen-abundant

Coumestan inhibits radical-induced oxidation of dna: Is hydroxyl a necessary functional groupΔ

Coumestan is a natural tetracycle with a C=C bond shared by a coumarin moiety and a benzofuran moiety. In addition to the function of the hydroxyl group on the antioxidant activity of coumestan, it is worth exploring the influence of the oxygen-abundant s

Microwave-assisted efficient synthesis of 2-hydroxydeoxybenzoins from the alkali degradation of readily prepared 3-aryl-4-.hydroxycoumarins in water

This paper describes an operationally simple, green and efficient approach for the synthesis of 2-hydroxydeoxybenzoins bearing diverse substituents from the microwave-assisted alkali degradation of 3-aryl- 4-hydroxycoumarins in water. The latter compounds

Hydroxycoumarins as selective MAO-B inhibitors

A series of 3-aryl-4-hydroxycoumarin derivatives was synthesized with the aim to find out the structural features for the MAO inhibitory activity and selectivity. Methoxy and/or chloro substituents were introduced in the 3-phenyl ring, whereas the positio

Antitrypanosomal and antioxidant properties of 4-hydroxycoumarins derivatives

In the present communication we prepared a series of six 4-hydroxycoumarin derivatives, isosters of quercetin, recognized as an antioxidant natural compound, with the aim of evaluating the antitrypanosomal activity against Trypanosoma cruzi, the parasite

Synthesis and cytotoxic activity of non-naturally substituted 4-oxycoumarin derivatives

Coumarins are a large family of natural and synthetic compounds exerting different pharmacological effects, including cytotoxic, anti-inflammatory or antimicrobial. In the present communication we report the synthesis of a series of 12 diversely substituted 4-oxycoumarin derivatives including methoxy substituted 4-hydroxycoumarins, methyl, methoxy or unsubstituted 3-aryl-4-hydroxycoumarins and 4-benzyloxycoumarins and their anti-proliferative effects on breast adenocarcinoma cells (MCF-7), human promyelocytic leukemia cells (HL-60), human histiocytic lymphoma cells (U937) and mouse neuroblastoma cells (Neuro2a). The most potent bioactive molecule was the 4-hydroxy-5,7- dimethoxycoumarin (compound 1) which showed similar potency (IC50 0.2-2 μM) in all cancer cell lines tested. This non-natural product reveals a simple bioactive scaffold which may be exploited in further studies.

Facile metal-free synthesis of 3-aryl-4-substituted coumarins from o-hydroxy carbonyl compounds

The intramolecular cyclization of the esters of salicylaldehyde, O-hydroxyacetophenones, methyl salicylate, and 2'-hydroxy chalcones by potassium hydroxide in pyridine leads to a short and convenient synthesis of 3,4-disubstituted coumarins. Twenty 3-phenyl coumarins were synthesized in 80-90% yields. No other by-product, such as 2-benzylchromone or-diketones, was observed the reactions. The mild reaction condition involves the removal of more acidic benzylic proton, which leads to a relatively cheap, nontoxic, metal-free method for the synthesis of 3-aryl-4-substituted coumarins. Copyrigh

A different route to 3-aryl-4-hydroxycoumarins

We herein report the simple and direct arylation of 4-hydroxycoumarins by photoinduced reaction with aryl halides (iodobenzene, iodonaphthalene, 4-iodoanisole, 2-iodoanisole). Good yields of 3,4-disubstituted coumarins were obtained in these reactions (>60%). Extension of the procedure to the reaction with o-dihalobenzenes leads to the synthesis of ring closure products which bear a tetracyclic aromatic-condensed ring system, although in lower overall yields (≈45%).

Synthesis of coumarins, 4-hydroxycoumarins, and 4-hydroxyquinolinones by tellurium-triggered cyclizations

Coumarins, 4-hydroxycoumarins, and 4-hydroxyquinolin-2(1H)-ones can be conveniently prepared by treatment of α-halocarboxylic acid esters of salicylaldehyde, o-hydroxyacetophenone, methyl salicylate, and methyl N-methyl- or N-phenylanthranilates with sodium or lithium telluride. Phenylketene formation competes with cyclization of the α-chlorophenylacetate ester of methyl salicylate as demonstrated by a trapping experiment with benzylamine. Elemental tellurium may be recovered and reused.