Synthesis of pyranobenzopyran using a catalytic amount of libf 4. Coumarin skelton holds substantial promise for further exploration because of its immense pharmacological potential. Onepot, fourcomponent synthesis of pyrano 2,3cpyrazoles catalyzed by sodium benzoate in aqueous medium hamzeh kiyania, heshmat allah samimib, fatemeh ghorbania and samira esmaielia aschool of chemistry, damghan university, 36715364, damghan, iran. Ammi visnaga also contains visnadin, a pyranocoumarin. The structures of the synthesized compounds were confirmed by spectral and elemental analysis. Basic plant taxonomy, basic essential oil chemistry, extraction, biosynthesis, and. Synthesis of 6methyl2substituted8h pyrano 2, 3e benzoxazol8one procedure. A diastereoselective synthesis of pyrano fused coumarins. The structure of carbohydratefused pyrano 3,2cpyranone, carbohybrid 12 was established by 1d and 2d nmr noe, cosy and hsqc experiments and comparing it with earlier spectral data.
A new series of 3,5bisarylidene4piperidones, as chal cone analogues carrying variety of aryl and heteroaryl groups, pyrazolo4,3cpyridines, pyridolo4,3cpyrimidines, and pyrido4,3cpyridines, carrying an arylidene moiety, and a series of pyrano 3,2cpyridines, as flavone and coumarin isosteres, were synthesized and screened for. Among them, compounds 5g, 6a, 6b, 6c, 6d and 6h exhibited more effective control than osthole against cucumber. Sciences, berhampur, orissa, india 2department of chemistry, vedica college of pharmacy, bhopal, mp, india. The details of the synthetic design and reaction optimization for the synthesis of these compounds can be obtained from the previous study. Synthesis of pyrano 3,2b1benzopyrans from dglycals. Abderrahim ben said, anis romdhane, nicolas elie, david touboul and hichem ben jannet affiliation. The synthesis of several coumarin mannich bases is described. Structureactivity relationships of synthetic coumarins as. An efficient synthetic approach towards benzob pyrano 2,3e1,4. It involves other methods which have been developed by pechmann claisen, knoevenagal, reformatsky reaction and wittig for the synthesis of pyronering moieties in coumarins.
L proline was also successfully applied as a neutral bifunctional catalyst for the condensation of aromatic aldehydes, malononitrile and barbituricor thiobarbituric acid in aqueous ethanol. Coumarins and related compounds from the medicinal plants of africa. Green, unexpected synthesis of biscoumarin derivatives as. Onepot, threecomponent synthesis of novel pyrano3,2 c. Coumarins regenerate after acidification or saturation by 2. The reaction between 5,7dihydroxy4substituted coumarin, malononitrile, and aromatic aldehydes in the presence of a catalytic amount of k2co3 as a basic catalyst leads to new pyrano 2,3h coumarin derivatives in good to excellent yields. Synthesis and evaluation of antiproliferative and src kinase inhibitory activities abha kathuria, a sarah jalal, a rakesh tiwari, b amir nasrolahi shirazi, b shilpi gupta, a shiv kumar, a keykavous parang, b, sunil k. Basedependent cascade synthesis of novel pyrano 3,2 c coumarin derivatives from baylishillman bromide. One pot synthesis of fused chromenopyranopyrimidines and. Current chemistry letters a facile and efficient protocol. Synthesis of 6methyl2substituted8h pyrano 2, 3e benzoxazol8ones procedure. Microwave assisted synthesis of pyrano 2, 3d pyrimidinone derivatives d. For instance, the negligent color variance prior to and after the irradiation of flindersine hampers its potential to serve as materials used in photochromic ophthalmic lenses. We synthesized a series of novel pyrrole and pyrazolesubstituted coumarin derivatives and evaluated their antifungal activity against six phytopathogenic fungi in vitro.
Yuan2 1department of radiation oncology, chongqing cancer institute and hospital and cancer center, chongqing, china 2department of clinical laboratory, chongqing the seventh peoples hospital, chongqing, china abstract series of novel coumarin derivatives i ad and ii ad. Coumarins have been synthesized by several methods. An efficient green method for the synthesis of novel functionalized pyrano 3,2c coumarins from a onepot threecomponent reaction of 4hydroxycoumarins, dialkylacetylenedicarboxylates and alkyl. Synthesis and cytotoxic activity of pyranocoumarins of the seselin. Multicomponent reaction of 4hydroxy coumarin, aromatic aldehydes, and sulfone derivatives catalyzed by piperidine has been accomplished for the synthesis of a series of novel pyrano 3,2c coumarin derivatives in ethanol under ultrasonic irradiations. In this work, a novel, convenient, and efficient approach to the synthesis of pyrano 2,3h coumarins has been reported based on the multicomponent reaction. An efficient annulation of phenolic acetates with acrylates in the presence of rh 2 oac 4 as catalyst and formic acid as reducing agent provides high yield of coumarin derivatives via ch bond activation.
Synthesis and evaluation of coumarin derivatives against. Their lipophilicity was determined experimentally by rptlc method. Much less works are devoted to the synthesis of coumarins containing. Onepot synthesis of novel pyrano fused coumarins catalyzed by zno nanoparticles. Regioselective synthesis of coumarin and quinolone. Pyrano coumarins containing a six membered ring attached to the coumarin moiety e. Synthesis and evaluation of coumarin derivatives against human lung cancer cell lines k. Synthesis and antihiv activity of new fused chromene derivatives derived from 2amino41naphthyl5oxo4h,5h pyrano 3,2 cchromene3carbonitrile najim a. Design, synthesis and antifungal activities of novel. New and facile synthesis of substituted pyrrole, pyridine. Coumarins are slowly hydrolyzed by dilute alkali and form yellow solution of coumaric cid salts. Synthesis and characterization of some new coumarins.
Synthesis of novel coumarin derivatives and its biological evaluations swayam sourav sahoo 1, smita shukla 2, subhangankar nandy 3 and himanshu bhusan sahoo 3 1department of pharma. The domino knoevenagel heterodielsalder reaction of the opropargylated salicylaldehydes and 4hydroxycoumarin leads to pyrano 2,3c coumarins 3 and pyrano 2,3cchromones 4 in high yield in the presence of cui as a lewis acid. During the synthesis of these compounds orthohydroxylation should respectively take. Annulated spiro heterocycles via aryl radical cyclization.
Synthesis and antiinflammatory activity of coumarin. Studies on pyranocoumarin 4acetic acid 54 chlorine atom. In the interest of synthesizing new coumarin ring systems for possible evaluation as biologically active compounds, we have described a synthesis of carboxymethyl coumarinsfromh ydroxylpyridine,carboxylicsystems, we wish to report here the synthesis of some benzofusedcoumarins. The onepot reaction between 5,7dihydroxy4methylcoumarin, dialkyl acetylenedicarboxylate and aromatic aldehydes catalyzed by sodium carbonate lead to the formation of a novel class of pyrano 2,3h coumarin derivatives.
Vahid et al 27 reported a solvent free onepot synthesis of coumarins from. March 2014 348 table i synthesis of pyrano chromenopyrimidines contd entry aldehydes 2aj chromeno pyrano pyrimidine 6aj yielda,b 9 2i s cho o o o n n nh2 6i s 79 10 2j o cho o o o n n o nh2 6j 76 aoverall yields starting from 4hydroxy coumarin, byields refer to the precipitated products table ii results of antibacterial screening of compounds 6aj and. Research article triphenylphosphine mediated synthesis of. Ir kbr spectra were recorded on a perkin elmer sp880 spec. Synthesis of pyrano 2,3,d pyrimidines under green chemistry. Earlier, coumarin was isolated by vogel in 1820 but he erroneously considered it as benzoic acid.
Synthesis and biological evaluation of fused pyrans. A new method for the synthesis of pyran fused coumarins by 3bromo4hydroxycoumarins as cyclic. Read synthesis and characterization of 2 h pyrano 3,2 c coumarin derivatives and their photochromic and redox properties, tetrahedron on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. Otf3catalyzed solventfree synthesis of pyrano 3,2c coumarins through a tandem additionannulation reaction between chalcones and 4hydroxycoumarins. The primary assay results demonstrated that some designed compounds displayed potent activities. Pdf a basecatalyzed, pseudofourcomponent reaction of 4hydroxycoumarin, two molecules of acetone, and amine towards the synthesis of pyrano2,3 c. Coumarin derivative an overview sciencedirect topics.
Synthesis and antihiv activity of new fused chromene. Synthesis of novel 2hpyrano2,3dthiazole6carbonitrile. Unexpected 3coumarinyl3pyrazolylpropanoic acids 3 and c4c4 chromenes 5 have been isolated instead of expected product 4 by the reaction of compound 2. Design, synthesis, and phenotypic profiling of pyrano. Substituted 4hydroxy 2h,5h pyrano 3,2c chromene 2,5 dionei have been prepared by 4hydroxy coumarin when treated with phosphorus oxychloride and zinc chloride. As shown in table 2, this method worked a wide variety of substrates. Synthesis of furanobenzopyran using a catalytic amount of libf 4.
Synthesis and evaluation of anticancer activity of 6. An efficient and simple synthesis of some 2amino3cyano4hpyran derivatives was developed by the onepot and threecomponent reaction of aldehydes, ethyl acetoacetate, and malononitrile in the presence of ammonia as catalyst at room temperature. The addition of naoac as a base increased the yield of the products. Sigmaaldrich offers a number of pyranocoumarin products. We have recently reported the synthesis of 7fluoro4methyl6nitro2oxo2h1benzopyran3carboxylic acid2 as a scaffold for solidphase synthesis of coumarins. Enhanced uptake, high selective and microtubule disrupting. Synthesis of pyrano 2,3,dpyrimidines derivatives in an aqueous media catalyzed by dahp. Coumarin and its derivatives considered as the most active classes of heterocycles, which possess a broad spectrum of biological activity. In all cases, the reaction was shown to exhibit high regioselectivity and form product 3 as main product. Pdf efficient synthesis of chromonylpyranoccoumarin. Akrawib, nadi eleyab, anke spannenbergd, christophe pannecouquee, and peter langerb. Various fused oxazine such as 44methoxyphenyl3,7dimethyl1,4dihydro5hpyrazolo 4.
Specific topics include synthesis and biological activity. Momprotected coumarins 7 29 and deprotection in a separate step resulted in virtually identical overall yields of coumarins 8 and did therefore not offer any advantage table1. Synthesis of angular furano or pyranofused coumarins. Synthesis and characterization of novel phthalimide. Ringclosingmetathesisbased synthesis of annellated. Pdf a onepot, threecomponent synthesis of new pyrano. Coumarin is prepared by treating the sodium salt of orthohydroxybenzqaldehyde with acetic anhydride. Synthesis of novel fused coumarine and naphtho2,1b. Sharma a, a department of chemistry, university of. Synthesis of 5amino7substituted phenyl2thioxo3,7dihydro2h pyrano 2,3dthiazole6carbonitrile 4al a. For the synthesis of furanocoumarins 3 and their ringexpanded oxepino analogues 11 the. Diazotized radical connects to 6 atom of coumarin in alkaline media.
Pyrano coumarins containing a six membered ring attached to the coumarin. A series of substituted aldehydes possessing either electronwithdrawing group or donating group reacted with malononitrile and 2thioxothiazolidin4one under the optimized conditions to give the. An ironcatalyzed route for the regioselective synthesis of 1,3 and 1,3,5substituted. Pdf onepot synthesis of novel pyranofused coumarins. Synthesis and pharmacological activities of pyrano2,3d. Synthesis of novel coumarin derivatives and its biological. A green and efficient protocol has been developed and a series of coumarin based pyrano 3,2cchromene derivatives 2 have been synthesized using multicomponent reaction mcr approach. All compounds were evaluated for their antiinflammatory and antioxidant activity and for their ability to inhibit in vitro lipoxygenase. Pdf a novel series of functionalized heterocyclic compounds containing the chromone skeleton was. A novel protocol for the synthesis of pyrano2,3hcoumarins in the. Synthesis and characterization of 2hpyrano3,2ccoumarin. Pdf multicomponent synthesis of pyrano2,3 c coumarins.
We provide a series of coumarin derivatives containing sulfone moiety of interest for biological screening tests. Onepot synthesis of novel pyrano fused coumarins catalyzed by zinc oxide nanoparticles article pdf available in heterocycles 897. I on reaction with acetic acid and phosphorous oxychlorideto give 3 acetyl 4hydroxy 2h,5h pyrano 3,2c chromene 2,5 dioneii. Synthesis of novel fused coumarine and naphtho2,1b pyrano 3,2 e1,2,4 triazolo1,5cpyrimidine derivatives volume.