- A convenient synthesis of 3-arylcoumarins from arylacetonitriles
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The condensation of salicylaldehydes with various arylacetonitriles catalyzed by anion-exchange resins such as Amberlite IRA 900, leads to the corresponding 3-arylcoumarins in good yields and selectivity.
- Mhiri,Ladhar,El Gharbi,Le Bigot
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- Photophysical investigation of 3-substituted 4-alkyl and/or 7-acetoxy coumarin derivatives-A study of the effect of substituents on fluorescence
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In the present work an array of novel substituted 2H-chromen-2-one (coumarin) derivatives has been subjected to photophysical analysis. Though the influence of the electron-donating groups such as amino, substituted amino, hydroxyl, alkoxy groups, etc. at position 7 of the coumarin ring system has been extensively studied, the luminescent properties of the coumarin moieties with an acetoxy substituent have not been explored. Herein it is attempted to study the variation of fluorescence behavior of substituted coumarin derivatives with change of nature and position of the substituents on the 2H-chromen-2-one skeleton. Effect of a methyl substituent at position 4 which imposes abnormal photophysical behavior to the chromenone unit has also been briefly described.
- Ranjith, Choorikkat,Vijayan,Praveen, Vakayil K.,Kumar, N.S. Saleesh
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- Dual Role of Oxoaldehydes: Divergent Synthesis of 3-Aryl- and 3-Aroylcoumarins
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A facile and efficient synthetic approach to various valuable 3-aryl- and 3-aroylcoumarins by the direct arylation and aroylation of coumarins with glyoxals in a metal-free manner is presented. The aryl glyoxal is for the first time recognized to serve as an aryl surrogate in addition to its role as an aroyl transfer reagent via a simple switch in reaction conditions. The approach accommodates a broad substrate scope and high yields of the two types of cross-coupling reactions starting from identical starting materials.
- Moazzam, Ali,Khodadadi, Meysam,Jafarpour, Farnaz,Ghandi, Mehdi
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p. 3630 - 3637
(2022/02/16)
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- Visible-light promoted oxidative cyclization of cinnamic acid derivatives using xanthone as the photocatalyst
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We have developed an efficient photocatalytic synthesis of coumarin derivativesviaa tandem double bond isomerization/oxidative cyclization of cinnamic acids. Inexpensive and stable xanthone was used as the photocatalyst, and readily available Selectfluor was used as the oxidant. This method tolerates a wide range of functional groups and offers excellent chemical yields in general. Besides, the photocatalytic oxidative cyclization of cinnamic acid esters gives dimerized lignan-type products.
- Zhao, Bin,Xu, Bo
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supporting information
p. 568 - 573
(2021/02/06)
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- Combatting AMR: A molecular approach to the discovery of potent and non-toxic rhenium complexes active against C. albicans-MRSA co-infection
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Antimicrobial resistance (AMR) is a major emerging threat to public health, causing serious issues in the successful prevention and treatment of persistent diseases. While the problem escalates, lack of financial incentive has lead major pharmaceutical co
- Crochet, Aurélien,Pavic, Aleksandar,Radakovic, Natasa,Roch, Paul,Sovari, Sara Nasiri,Zobi, Fabio
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supporting information
(2021/09/28)
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- Zn(II)-Catalyzed One-Pot Synthesis of Coumarins from Ynamides and Salicylaldehydes
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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.
- Yoo, Huen Ji,Youn, So Won
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p. 3422 - 3426
(2019/05/10)
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- Pd-catalysed carbonylative annulation of salicylaldehydes with benzyl chlorides using N-formylsaccharin as a CO surrogate
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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.
- Yadav, Vinod K.,Srivastava, Vishnu P.,Yadav, Lal Dhar S.
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supporting information
p. 16281 - 16286
(2018/10/04)
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- KMnO4/AcOH-mediated C3-selective direct arylation of coumarins with arylboronic acids
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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.
- Yuan, Jin-Wei,Yang, Liang-Ru,Yin, Qiu-Yue,Mao, Pu,Qu, Ling-Bo
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p. 35936 - 35944
(2016/05/19)
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- Regioselective α-arylation of coumarins and 2-pyridones with phenylhydrazines under transition-metal-free conditions
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A facile regioselective metal-free direct α-arylation of coumarins and 2-pyridones is achieved by the reaction of coumarins and 2-pyridones with phenylhydrazine in good yields. The reaction proceeds at room temperature under mild conditions using inexpensive reagents and without the need for step intensive activating groups. The methodology is operationally simple, practically viable and also allows the coupling of similar nitrogen heterocycle aza-coumarins without prerequisite N-protection.
- Chauhan, Parul,Ravi, Makthala,Singh, Shikha,Prajapati, Prashant,Yadav, Prem P.
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p. 109 - 118
(2016/01/09)
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- Synthesis and Evaluation of Coumarin-Resveratrol Hybrids as 15-Lipoxygenaze Inhibitors
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A series of coumarin-resveratrol hybrids, 3-arylcoumarin derivatives 3a-u, were synthesized through the intermolecular condensation reaction of various salicylaldehydes and phenylacetic acids in the presence of 1,4-diazabicyclo[2.2.2]octane under solvent-free conditions. All the synthesized compounds were screened for their inhibitory potency against soybean 15-lipoxygenase. Among them, three compounds (3c, 3j, and 3q) showed good enzyme-inhibitory activities. GRAPHICAL ABSTRACT.
- Rahmani-Nezhad, Samira,Khosravani, Leila,Saeedi, Mina,Divsalar, Kouros,Firoozpour, Loghman,Pourshojaei, Yaghoub,Sarrafi, Yaghoub,Nadri, Hamid,Moradi, Alireza,Mahdavi, Mohammad,Shafiee, Abbas,Foroumadi, Alireza
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supporting information
p. 751 - 759
(2015/10/29)
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- Base-promoted synthesis of coumarins from salicylaldehydes and aryl-substituted 1,1-dibromo-1-alkenes under transition-metal-free conditions
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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.
- Liu, Jianming,Zhang, Xin,Shi, Lijun,Liu, Muwen,Yue, Yuanyuan,Li, Fuwei,Zhuo, Kelei
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supporting information
p. 9887 - 9890
(2014/08/18)
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- Magnetically retrievable nano crystalline nickel ferrite- catalyzed aerobic, ligand-free C-N, C-O and C-C cross-coupling reactions for the synthesis of a diversified library of heterocyclic molecules
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A new nickel ferrite nano-crystal-catalyzed, ligand-free strategy for the construction of C-N, C-O, and C-C bonds is presented, in which easily available nitrogen and oxygen nucleophiles, aryl/heteroaryl halides and arylboronic acids are used for the cross-coupling reactions. The reactions can be performed at low catalyst loadings with excellent functional group tolerance and chemoselectivity. A variety of functional groups are compatible with the reaction conditions, including nitro, methoxy, as well as acid- and base-sensitive heteroaromatic groups. This unprecedented chemistry nicely complements classical methods for the N-arylation of amines/heteroamines, the O-arylation of phenols/hydroxycoumarins and biaryl/heteroaryl synthesis. The low cost, easy to handle nature and the simplicity of this catalytic system render the method competitive with comparable copper- and palladium-based protocols which require the presence of sophisticated ligands. Nickel ferrite magnetic nanoparticles were prepared by a simple hydrothermal method and characterized by using XRD, TEM image, energy dispersive X-ray analysis, XPS and FT-IR. The easy recovery of the catalyst and high yield of the products make the protocol attractive, sustainable and economic. The catalyst was reused for five cycles with almost unaltered catalytic activity.
- Paul, Sanjay,Pradhan, Koyel,Ghosh, Sirshendu,De,Das, Asish R.
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p. 1301 - 1316
(2014/05/06)
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- A general palladium-catalyzed carbonylative synthesis of chromenones from salicylic aldehydes and benzyl chlorides
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Cute CO! An interesting and straightforward procedure for the carbonylative synthesis of chromenones from readily available salicylic aldehydes and benzyl chlorides has been developed (see scheme; DPPP=1,3-bis(diphenylphosphino) propane). In the presence of a palladium catalyst, various coumarins were produced in good to excellent yields. Copyright
- Wu, Xiao-Feng,Wu, Lipeng,Jackstell, Ralf,Neumann, Helfried,Beller, Matthias
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p. 12245 - 12248
(2013/09/23)
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- Synthesis of 3-arylcoumarins through N-heterocyclic carbene catalyzed condensation and annulation of 2-chloro-2-arylacetaldehydes with salicylaldehydes
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The condensation reaction of 2-chloro-2-arylacetaldehyde with salicylaldehyde catalyzed by N-heterocyclic carbene (NHC) leading to 3-arylcoumarin was studied. A number of 3-arylcoumarin derivatives were obtained in good to excellent yields via this umpolung reaction. This reaction is facile and experimentally simple and mild.
- Jiang, Yuansong,Chen, Wanzhi,Lu, Weimin
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p. 3669 - 3676
(2013/05/08)
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- 3-phenylcoumarins as inhibitors of HIV-1 replication
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We have synthesized fourteen 3-phenylcoumarin derivatives and evaluated their anti-HIV activity. Antiviral activity was assessed on MT-2 cells infected with viral clones carrying the luciferase gene as reporter. Inhibition of HIV transcription and Tat function were tested on cells stably transfected with the HIV-LTR and Tat protein. Six compounds displayed NF-κB inhibition, four resulted Tat antagonists and three of them showed both activities. Three compounds inhibited HIV replication with IC50 values 25 μM. The antiviral effect of the 4-hydroxycoumarin derivative 19 correlates with its specific inhibition of Tat functions, while compound 8, 3-(2-chlorophenyl) coumarin, seems to act through a mechanism unrelated to the molecular targets considered in this research.
- Olmedo, Dionisio,Sancho, Rocio,Bedoya, Luis M.,Lopez-Perez, Jose L.,Del Olmo, Esther,Munoz, Eduardo,Alcami, Jose,Gupta, Mahabir P.,Feliciano, Arturo San
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p. 9245 - 9257
(2013/01/14)
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- One-pot greener protocol for the synthesis of substituted coumarins
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An expeditious one-pot procedure for the synthesis of substituted coumarins under microwave irradiation is accounted. The method describes an easy and fast method for the synthesis of substituted acetoxy coumarins which are very good fluorophores for medical as well as industrial applications. It makes use of easily available reagents such as triethylamine and acetic anhydride as catalyst. The method finds good applications for the synthesis of multisubstituted coumarins.
- Ranjith, Choorikkat,Paul, Nidhin,Vijayan
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experimental part
p. 235 - 238
(2011/11/30)
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- Synthesis of 3-arylcoumarins via Suzuki-cross-coupling reactions of 3-chlorocoumarin
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A convenient and innovative protocol for an efficient synthesis of different substituted 3-arylcoumarins is reported. The developed synthetic route involves a Pd-catalyzed cross-coupling reaction using a catalytic complex Pd-salen. Under these conditions a series of different substituted boronic acids have been successfully coupled to a coumarin halide to afford novel coumarins in good yields.
- Matos, Maria Joao,Vazquez-Rodriguez, Saleta,Borges, Fernanda,Santana, Lourdes,Uriarte, Eugenio
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experimental part
p. 1225 - 1227
(2011/03/22)
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- High temperature zincation of functionalized aromatics and heteroaromatics using TMPZnCl·LiCl and microwave irradiation
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A wide range of functional aryl and heteroaryl zinc reagents have been efficiently prepared via regio- and chemoselective zincation using TMPZnCl·LiCl and microwave irradiation. Sensitive functional groups like esters are compatible with the high temperat
- Mosrin, Marc,Monzon, Gabriel,Bresser, Tomke,Knochel, Paul
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supporting information; experimental part
p. 5615 - 5617
(2010/01/31)
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- A CONVENIENT SYNTHESIS OF 3-ARYL COUMARINS
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A new, convenient, one-step synthesis od 3-aryl coumarins from 2-fluorobenzaldehyde and aryl acetic acids is reported.
- Ming, Yang,Boykin, David W.
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p. 3229 - 3231
(2007/10/02)
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