2555-22-8

Usage

InChI:InChI=1/C16H12O3/c1-18-13-8-7-12-9-14(11-5-3-2-4-6-11)16(17)19-15(12)10-13/h2-10H,1H3

Upstream product

• 150-19-6 O-methylresorcine 
• 5841-70-3 phenyl(formyl)acetonitrile 
• 5451-83-2 acetic acid 3-methoxyphenyl ester 
• 73591-12-5 3-benzoyloxy-2-phenyl-acrylonitrile 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 1555-80-2 phenylacetic anhydride 
• 2431-96-1 N,N-diethylphenylacetamide 
• 20878-92-6 (E)-2,4-dimethoxy-α-phenylcinnamic acid 
• 103-82-2 phenylacetic acid 
• 7664-93-9 sulfuric acid 
• 1240249-56-2 C₁₆H₁₄O₄ 
• 591-50-4 iodobenzene 
• 20300-59-8 7-methoxycoumarin-3-carboxylic acid 
• 932-87-6 1-Bromo-2-phenylacetylene 

Downstream Products

• 213844-39-4 7-methoxy-2,2-dimethy-3-phenyl-2H-chromene 

Relevant academic research and scientific papers

Chlorophyll-catalyzed photochemical regioselective coumarin C-H arylation with diazonium salts

This communication describes the development of a mild method for the cross-coupling of the C3-position of coumarin with an array of diazonium salts mediated by chlorophyll as a biocatalyst via visible light catalysis. A natural pigment such as chlorophyll is used as a green photosensitizer and environmentally benign catalyst. This general and easy procedure provides a transition-metal-free alternative for the formation of 3-aryl coumarin derivatives at room temperature with good to excellent yields. This journal is

Zn(II)-Catalyzed One-Pot Synthesis of Coumarins from Ynamides and Salicylaldehydes

A highly efficient and straightforward synthesis of diversely substituted coumarins from ynamides and salicylaldehydes in the presence of Zn(II) catalyst has been developed. The sulfonamide moiety of ynamides was successfully recycled in this process, serving as an effective traceless directing group for high regioselectivity in the bond-forming event. The advantages of this protocol are good functional group tolerance, broad substrate scope, simple and high-yielding reaction, recovery/reuse of the sulfonamides, low catalyst loading of inexpensive catalyst, and, by these merits, a more cost-effective and greener process.

Pd-catalysed carbonylative annulation of salicylaldehydes with benzyl chlorides using N-formylsaccharin as a CO surrogate

A convenient and highly efficient Pd-catalysed carbonylative annulation of salicylaldehydes with benzyl chlorides to afford the corresponding 3-arylcoumarins in good to excellent yields has been developed. Importantly, the protocol utilizes a commercially available, low cost, solid and easy to handle N-formylsaccharin as an alternative to the highly toxic CO gas.

A transition-metal-free fast track to flavones and 3-arylcoumarins

A highly regioselective and transition-metal free one-pot arylation of chromenones with arylboronic acids has been achieved employing K2S2O8. The procedure consists of a sequence of some reactions including an arylation/decarboxylation cascade and proceeds well in aqueous media to afford biologically interesting flavones and 3-arylcoumarins. This method exhibited excellent selectivity and functional group tolerance under mild conditions. The reaction also showed perfect efficacy for the preparation of styryl coumarins.

KMnO4/AcOH-mediated C3-selective direct arylation of coumarins with arylboronic acids

An efficient protocol for KMnO4/AcOH-mediated dehydrogenative direct radical arylation of coumarins with arylboronic acids to afford 3-arylcoumarin derivatives is described. A similar reaction system is also applicable to the 3-arylation of quinolinone derivatives. These KMnO4/AcOH-mediated coupling reactions occur regioselectively at the C3 position of coumarins and quinolinones. Some notable features of this method are high efficiency, moderate to good yield, and a broad group tolerance.

3-aryl coumarin derivatives and preparation method thereof

The invention discloses 3-aryl coumarin derivatives (I) and (II) and a preparation method thereof and belongs to the field of organic chemistry. According to the method, a substituent coumarin derivative and substituent arylboronic acid are used as raw materials and changed into a solvent with acetic acid under the catalysis of Mn(OAc)3 to synthesize the 3-aryl coumarin derivatives. The synthetic method has the advantages that the raw materials are low in price and easy to get, reaction conditions are mild, the yield is high, operation is convenient, and industrial production is facilitated. The derivatives have potential application in the fields of materials, chemical industry, medicine and the like. A new way is provided for synthesis of the 3-aryl coumarin derivatives. (Please see the description for the formulas I and II).

Design and synthesis of ERα/ERβ selective coumarin and chromene derivatives as potential anti-breast cancer and anti-osteoporotic agents

Several new coumarin and chromene prototype derivatives have been synthesised and evaluated for their ERα and ERβ selective activity. Coumarin prototype compounds 18 & 19 were found to be ERα selective and the most active, exhibiting potential antiproliferative activity against both ER +ve & ER -ve breast cancer cell lines. The surprise finding of the series, however, are the novel prototype III chromenes 45 & 46, with aroyl substitution at the 6th position. Both the compounds have shown potent antiproliferative activity against both the breast cancer cell lines, promote alkaline phosphatase activity, enhance osteoblast mineralization in vitro, significantly decrease ERE-ERα dependent transactivation and induce ERβ activity. This specific upregulation of ERβ isoform activity of compound 45 may be responsible for the antiosteoporotic activity at picomolar concentration. In addition, both the compounds were also devoid of any estrogenic activity, which correlates to their antiestrogenic behaviour in the two breast cancer cell lines. Assessment of selectivity using specific SiRNAs for ERα and ERβ revealed that most of the compounds showed ERα and ERβ-mediated action, except compound 28, which showed selectivity to ERα only. Computational docking analysis of active compounds 18 and 45 was conducted to correlate the interaction with the two receptors and it was found that the docked conformations of the coumarin prototype, compound 18 at ERα and ERβ active sites were more or less superimposable on each other. However, the unique orientation of the aminoalkoxy side chain of novel chromene (prototype III) compound 45 in the ERβ binding cavity may be responsible for its potential biological response. The Royal Society of Chemistry.

A complete switch of the directional selectivity in the annulation of 2-hydroxybenzaldehydes with alkynes

Controlling reaction selectivity is an eternal pursuit for chemists working in chemical synthesis. As part of this endeavor, our group has been exploring the possibility of constructing different natural product skeletons from the same simple starting mat

Base-promoted synthesis of coumarins from salicylaldehydes and aryl-substituted 1,1-dibromo-1-alkenes under transition-metal-free conditions

Facile synthesis of coumarin via the tandem reaction of salicylaldehyde with aryl-substituted 1,1-dibromo-1-alkene was developed. This new protocol proceeds smoothly under mild and transition-metal-free conditions, it allows rapid access to coumarins containing various heteroatoms that are more difficult to prepare by traditional methods. Based on the isolated intermediate of 4-(diethylamino)-3-phenylchroman-2-one and detailed mechanistic studies, a credible tandem pathway was proposed.

Palladium catalyzed dehydrogenative arylation of coumarins: An unexpected switch in regioselectivity

A new regioselective α-arylation of coumarins with unactivated simple arenes via a palladium-catalyzed twofold C-H functionalization is devised. This method offers an attractive new approach to synthesis of a wide variety of 3-arylcoumarins from readily accessible starting materials. This journal is The Royal Society of Chemistry 2013.