3 aryl coumarins pdf

Crystalline 3 4 aryl 1,2, 3 triazol1yl coumarins atcs were prepared from commercial materials using a fourcomponent methodology as a key step. Cheng zhao 1a,1b, liang lingling 1a,1b, miao yanqing 1a,1b. It is also known to found in bark and timber of sri lankan endemic plant mesua thwaitesii. An efficient and general protocol for a rapid synthesis of different substituted 3 aryl coumarins is reported. Onepot preparation of 4aryl3bromocoumarins from 4aryl. In the present work, a feasible and environmentally friendly route to the title compounds was. The bromocyclization of aryl 3 aryl 2propynoate 2 with tbab and na 2 s 2 o 8 proceeds via a bromoradical addition to the triple bond to form very reactive vinyl radical i. Their activities can include antiinflammatory, antispasmodic, antiedematous, and vascular tonic effects. Neoflavones are derived from the 4phenylcoumarin or 4aryl coumarin backbone c 15 h 12 o 2. The fluorescence lifetimes of coumarins are determined in different solvents. Pdf efficient and general synthesis of 3aryl coumarins using. A series of substituted phenyl acetic acids have been successfully reacted with substituted 2hydroxy benzaldehydes to afford 3 aryl coumarins in good to excellent. Coumarin can be prepared by a number of name reactions, with the perkin reaction between salicylaldehyde and acetic anhydride being. Various 3 4styryl6 aryl pyridin2yl coumarins 4af and 3 6styryl4 aryl pyridin2yl coumarins 5af have been synthesized by the reaction of 3 coumarinoyl methyl pyridinium salt 1 with pentadienones 2af and 3af respectectively in the presence of ammonium acetate in refluxing acetic acid.

A fast and highly efficient green method for synthesizing. Strong intermolecular interactions in crystalline 34. Bf3et2omediated electrophilic cyclization of aryl alkynoates using nsulfanylsuccinimides the journal of organic chemistry. Synthesis of 3phenylbenzog1benzopyrano4,3eindazol8. Effect of intermolecular interactions on the formation of. Electron deficient phenols gave low yield of coumarin products, restricting the utility of this procedure 41. The yields of 3arylcoumarins range from 7% 98% with the maximum yield of 98% obtained for 6nitro3 4nitrophenyl coumarin.

Twenty 3phenyl coumarins were synthesized in 8090% yields. Synthesis, characterization and antimicrobial activity of. The synthesis of coumarin and pyrazolyl substituted pyrido3,2c coumarins has been carried out by reacting various 4hydroxy coumarins with appropriate 7hydroxy4methyl831phenyl3aryl1hpyrazol4ylacryloylcoumarin under krohnkes reaction condition. Most of these coumarins are mono or deoxygenated in the aromatic ring 16. A series of substituted phenyl acetic acids have been successfully reacted with substituted 2hydroxy benzaldehydes to afford 3aryl.

For instance, 3phenyl substituted coumarin derivatives displayed strong. The in vitro antioxidant and soybean lipoxygenase inhibitory activity of the new compounds has been evaluated. The order of reactivity of the pseudohalide substituents in the coumarins was found to be 4otf. Synthesis of coumarin and pyrazolyl substituted pyrido3,2c. Results and discussion the compounds 3ao have been synthesized in good yield by reacting 3coumarinoyl methyl pyridinium bromides 1ac with appropriate 2arylidene tetralone 2ae under krohnkes reaction condition. Onepot twostep synthesis of 3iodo4aryloxy coumarins. Oct 17, 2016 in this work, the theoretical study of global. Coumarins were synthesized form variety of electron rich phenols and electron rich cinnamates under mild reaction condition in the presence of trifluoroacetic acid at room temperature. A metalfree, radical reaction has been performed with tertbutylhydroperoxide in water, chlorobenzene, for 20 h and at 100 c, and in sealed tube. Us3869469a us226528a us22652872a us3869469a us 3869469 a us3869469 a us 3869469a us 226528 a us226528 a us 226528a us 22652872 a us22652872 a us 22652872a us 3869469 a us3869469 a us 3869469a authority us.

Coumarin is a therapeutic agent, found as a naturally occurring secondary metabolite in plants, bacteria, fungi, essential oils and can also be chemically synthesized. Convenient synthesis of 3 vinyl and 3 styryl coumarins. Us patent for 3aryl7pyrazolylcoumarins patent patent. Cyanomethylated coumarins were synthesized via cyanomethylation and cyclization of aryl alkynoates using cheap and available reagent acetonitrile as the cyanomethyl source in the presence of tbpb tertbutyl peroxybenzoate under transitionmetalfree conditions. The formation of specific stacked associates in the crystal of 34. Bf3et2omediated electrophilic cyclization of aryl alkynoates using nsulfanylsuccinimides the journal of organic chemistry acs publications.

Et2omediated electrophilic cyclization of aryl alkynoates using nsulfanylsuccinimides wenchao gao, tao liu, bing zhang, xing li, wenlong wei, qiang liu, jun tian, and honghong chang. The 3 1acyl5 aryl 3 pyrazolinyl coumarins turned to be photosensitive compounds and undergo photolysis under irradiation in the range of 310465 nm. Microwave assisted synthesis and biological activity of 3arylfuro3. Synthesis of 3aryl coumarin derivatives under ultrasound irradiation in the presence of thf and potassium car bonate. A fast and highly efficient green method for synthesizing 3aryl coumarin derivatives from salicylaldehyde and phenyl acetyl chloride in the presence of. Coumarins have been isolated from different families of plant kingdom like clusiaceae, umbelliferae and rutaceae. Efficient and general synthesis of 3aryl coumarins using. These coumarin derivatives are found to be effective fluorophores and show high values of quantum yields of fluorescence both in nonpolar and in polar solvents. A novel synthesis of 3aryl coumarins and evaluation of. A series of different substituted phenyl acetic acids have been successfully reacted. One natural compound that has been studied is coumarin, and the factors which makes it a good candidate for an antiviral drug, are its role in targeting various cellular pathways, inhibiting the growth and replication of viruses. Nine different 3aryl coumarins have been prepared by a onepot method using ultrasound irradiation and the re sults are summarized in the table 1. Department of chemistry, university of kalyani, kalyani 741 235, india. Strong intermolecular interactions in crystalline 3 4.

Direct radical trifluoromethylthiolation and thiocyanation of aryl alkynoate esters. Competitive 3,3 sigmatropic rearrangement of aryl propargyl ether moiety vs propargyl vinyl amine part in 6n4. Facile metalfree synthesis of 3aryl4substituted coumarins from. Onepot preparation of 4aryl3bromocoumarins from 4aryl2. The intramolecular cyclization of the esters of salicylaldehyde, o hydroxyacetophenones, methyl salicylate, and 2.

The mild reaction condition involves the removal of more acidic benzylic proton, which leads to a relatively cheap, nontoxic, metalfree method for the synthesis of 3aryl4substituted coumarins. Us3242177a us362935a us36293564a us3242177a us 3242177 a us3242177 a us 3242177a us 362935 a us362935 a us 362935a us 36293564 a us36293564 a us 36293564a us 3242177 a us3242177 a us 3242177a authority us united states prior art keywords coumarin compounds compounds aryl coumarin brightening prior art date 19630511 legal status the legal status is an. Results and discussion as we already demonstrated that aryl vinyl ketones could be cyclized to indanones in the presence of acidic zeolites,19 we expected that homologous aryl propynoates would react in a similar way. The obtained 3 bromo4phenylcoumarin was transformed into 4phenylcoumarin. Synthesis of some 31aryl9,10dihydro4azaphenanthren. Firstly by treatment with hydrochloric acid in ethanol and.

Convenient synthesis of 3vinyl and 3styryl coumarins. Facile onepot synthetic access to libraries of diversely substituted 3 aryl alkyl coumarins using ionic liquid il or conventional basesolvent, and an ilmediated approach to novel coumarin bearing diarylethynes. The first neoflavone isolated from natural sources was calophyllolide from calophyllum inophyllum seeds 1951. Synthesis, spectroscopy and electrochemistry of new 35. General and efficient route for the synthesis of 3,4. This method provides a new strategy toward the synthesis of 3 cyanomethylated coumarins via a domino radical addition5exo cyclizationester migration cascade reaction in moderate to good yields at room temper. The effects of solvent and ph factor on the absorption and fluorescence maxima are also studied. A fast and highly efficient green method for synthesizing 3 aryl coumarin derivatives from salicylaldehyde and phenyl acetyl chloride in the presence of tetrahydrofuran and k 2 co 3 using ultrasound irradiation is reported. Coumarins coumarins of different kinds are found in many plant species and have widely divergent actions. A series of substituted phenyl acetic acids have been successfully reacted with substituted 2hydroxy benzaldehydes to afford 3 aryl coumarins in good to excellent yields. Similarly, reaction of 2hydroxybenzaldehydes 1fm and 2hydroxybenzophenones 1np with phenylacetic acids 2ad gives the corresponding 3arylcoumarins 3fm and 3aryl4phenylcoumarins 3np respectively. A ph 3 pi 2et 3 nmediated onepot twostep esterificationcyclization provides 3 aryl coumarins and 3 aryl 4methylcoumarins from aryl acetic acids containing a steric or reactive group and 2hydroxybenzaldehydes or 2. Pdf coumarins occupy an important place in the realm of natural products and synthetic organic chemistry. For the substrates with various substituents on benzene ring, the reaction proceeded smoothly to give the corresponding products in.

The mild reaction condition involves the removal of more acidic benzylic proton, which leads to a relatively cheap, nontoxic, metalfree method for the synthesis of 3 aryl 4substituted coumarins. Neoflavones are derived from the 4phenylcoumarin or 4 aryl coumarin backbone c 15 h 12 o 2. Various 4 aryl 3 bromocoumarins were smoothly obtained in moderate yields in one pot by treating 3 aryl 2propynoic acids with diaryliodonium triflates and k2co3 in the presence of cucl, followed by the reaction with tetrabutylammonium bromide tbab and na2s2o8. The yield of 32,4dini trophenylcoumarin is also high. Jan 27, 2018 b synthesis of 3aroyl coumarins 9 from the reaction of coumarins, or coumarin3carboxylic acids with benzaldehydes, benzyl alcohols, and styrenes. General procedure for the synthesis of 3 1 aryl 9,10dihydro4azaphenanthren 3 yl coumarins 3ao in a 100 ml round bottom flask equipped with a dropping funnel, condenser, guard tube and magnetic needle an appropriate 3 coumarinoyl methyl pyridinium salt 1a. Palladiumcatalyzed siteselective crosscoupling reactions of 3 bromo4trifloxycoumarin or 3 bromo4tosyloxycoumarin provide an efficient and facile route for the synthesis of 3,4disubstituted coumarins, which include 3,4diarylcoumarins, 3 amino4arylcoumarins, and 3 aryl 4aminocoumarins. Novel c7substituted coumarins as selective monoamine. Abstract two series of novel coumarin derivatives, substituted at 3 and 7 positions with aminoalkoxy groups, are synthesized, characterized. Microwaveassisted synthesis and evaluation of antimicrobial activity of 3 3 s aryl and sheteroaromaticacryloyl2hchromen2one derivatives olayinka o. Abstract the near uv absorption spectra and fluorescence spectra of new coumarin dyes and pyrazolines synthesized in our laboratories are investigated in solution.

Ultrasoundassisted solventfree parallel synthesis of 3. Facile onepot synthetic access to libraries of diversely substituted 3 aryl alkyl coumarins using ionic liquid il or conventional basesolvent, and an ilmediated approach to novel coumarinbearing diarylethynes. It has been used a sunscreen, a fluorescence indicator and as. A facile, ecofriendly, onepot protocol for the synthesis of substituted 3 phenylfuro 3,2c coumarins from insitu generated. Link, who pioneered the isolation and characterization of bis hydroxycoumarin dicoumarol from sweet clover, concluded that the minimal requirements for anticoagulant activity are 4hydroxy group, a 3substituent, and a bis molecule chen et al, 2001.

Mild and facile synthesis of 3 trifluoromethylthiolated and 3 thiocyanated coumarins yaofu zeng, donghang tan, yunyun chen, wenxin lv, xuge liu, qingjiang li, honggen wang school of pharmaceutical sciences, sun yatsen university, guangzhou 56. Coumarin and 4hydroxycoumarin do not possess anticoagulant activity. The use of cyanuric chloride 2,4,6trichloro1,3,5triazine and n methyl morpholine enables an efficient and general protocol for a rapid synthesis of substituted 3aryl coumarins. Jan 27, 2020 various natural compounds including herbal products and plant extracts have been investigated for their antiviral activities against several viruses 11, 12, 14. Cyclization of diethyl ester 2 to ethyl coumarins 3 ester 1 eethyl 2bromo 3 2methoxymethoxyphenylacrylate 3 was converted into ethyl coumarin 3 carboxylate 1 via two steps. Novel 3arylcoumarin derivatives have been synthesized via a new methodology. General papers arkivoc 2010 xi 2838 issn 15517012 page 28 arkat usa, inc. The use of cyanuric chloride 2,4,6trichloro1, 3,5triazine and nmethyl morpholine enables an efficient and general protocol for a rapid synthesis of substituted 3 aryl coumarins. Coumarins occupy an important place in the realm of natural products and synthetic organic chemistry. Fluorescent coumarin dyes emitting red light and exhibiting large stokes shifts can be used in two. General procedure for the synthesis of 3arylfuro3,2ccoumarins 4al.

Twenty 3 phenyl coumarins were synthesized in 8090% yields. Synthesis and biological evaluation of 3arylcoumarins as potential. A visiblelightpromoted, mild, and direct cyanomethylation of aryl alkynoates has been developed. Synthesis of coumarin and pyrazolyl substituted pyrido3,2. Applications of coumarins as cardiovascular and anticancer agents.

Direct radical trifluoromethylthiolation and thiocyanation of. Cyanomethylation and cyclization of aryl alkynoates with. Synthesis and spectral characterization of some 31aryl9. Pdf synthesis of 3aryl coumarin derivatives using ultrasound.

Synthesis of 3aryl coumarin derivatives using ultrasound. Synthesis, characterization and antimicrobial activity of some 4 aryl 2,6di coumarin 3 ylpyridines. Taking account the possibility of genetic polymorphism over coumarin. Pdf efficient and general synthesis of 3aryl coumarins. Synthesis of 3 styryl coumarins 4 by palladium crosscoupling between 3 vinyl coumarins 2 and aryl halidesa entry compd r1 r2 ar palladium catalyst phosphine aromatic halide base yield % 1 4a h h ph pdoac2 pph3 c. A convenient onepot synthesis of 4methyl3phenyl, 3aryl. A fast and highly efficient green method for synthesizing 3 aryl coumarin derivatives from salicylaldehyde and phenyl acetyl chloride in the presence of tetrahydrofuran and k2co3 using ultrasound irradiation is reported.

A fast and highly efficient green method for synthesizing 3 aryl coumarin derivatives from. The mass spectrum of compound 3a was recorded on a shimadzu qp 2010 spectrometer. Microwave assisted synthesis and biological activity of 3. A fast and highly efficient green method for synthesizing 3aryl coumarin derivatives from salicylaldehyde and phenyl acetyl chloride in the presence of tetrahydrofuran and k 2co 3. A novel synthesis of 3aryl coumarins and evaluation of their. Nwinyib achemistry department, college of science and technology, covenant university, ota. Page 283 synthesis of some 3 1 aryl 9,10dihydro4azaphenanthren 3 yl coumarins niraj h patel, anil k patel, chirag v patel, apoorva a patel, and dinker i brahmbhatt department of chemistry, sardar patel university, vallabh vidyanagar388 120, gujarat, india email. Numerous research reports have indicated the coumarin nucleus as a potential candidate for development of antiinflammatory drugs. The synthesis of coumarin and pyrazolyl substituted pyrido 3,2c coumarins has been carried out by reacting various 4hydroxy coumarins with appropriate 7hydroxy4methyl8 3 1phenyl 3 aryl 1hpyrazol4ylacryloyl coumarin under krohnkes reaction condition.

No other byproduct, such as 2benzylchromone or b diketones, was observed the reactions. Parallel synthesis of 3arylcoumarins using nacylbenzotriazoles. The oarylation of 3 aryl 2propynoic acid 1 with diaryliodonium triflate in the presence of k 2 co 3 and cucl occurs to form aryl 3 aryl 2propynoate 2 1st step. In the first method different 3arylfuro3,2ccoumarins 4al have been synthesized by reacting various 4hydroxy coumarins 1ad with appropriate 2aryl1nitro ethenes 2ac under nef reaction condition, while in the second method the same target compounds have been synthesized by reacting various 4hydroxy coumarins 1ad with. Synthesis and biological activities of 3aryl coumarin. A novel synthesis of 3aryl coumarins and evaluation of their antioxidant and lipoxygenase inhibitory activity. Many 3 2pyridyl and 3 3 pyridyl coumarins are known for their useful bioactivities viz. Various phytoconstituents such as umbelliferone, scopoletin, columbiatnetin, visniadin, marmin, and many more derived from coumarin nucleus are found to have potent antiinflammatory as well as antioxidant activities.

Facile metalfree synthesis of 3aryl4substituted coumarins. The resulting 3 sulfenylated coumarins can be readily transformed to 3 sulfinylated or 3 sulfonylated coumarins under different oxidation conditions. Synthesis and biological activities of 3 aryl coumarin derivatives. Ultrasound assisted reactions have resulted in better yields and. Ph3pi2mediated synthesis of 3arylsubstituted and 3,4. Onepot preparation of 4 aryl 3 bromocoumarins from 4 aryl 2propynoic acids with diaryliodonium salts, tbab, and na2s2o8 teppeisasaki1. Formation of esters 4 and 5 and benzofuran 6 is also observed. The wellknown natural compound containing coumarin nucleus is 7hydroxycoumarin umbelliferone and is found in carrots, coriander and garden angelica. Pdf an efficient and general protocol for a rapid synthesis of different substituted 3aryl coumarins is reported. Aryl coumarin derivatives bearing aminoalkoxy moiety as multi.