Design and microwave assisted synthesis of coumarin derivatives as pde inhibitors article pdf available february 2016 with 207 reads how we measure reads. Pdf microwaveassisted synthesis of coumarinbased 5,6. There are some useful methods to obtain coumarin derivatives. Phloroglucinol, pyrogallol, phenol and mmethyl phenol substrates were reacted with ethyl acetoacetate under microwave irradiation 250 w in presence of nanocrystalline sulfatedzirconia catalyst under solvent free conditions. The structures of all the compounds synthesized have been supported by analytical and spectral data. These compounds were analyzed for phosphodiesterase pde inhibition indirectly by motility pattern in human spermatozoa. Microwaveassisted solvent free synthesis of hydroxy. Microwaveassisted synthesis and antioxidant properties of. Schiff base is a potential target to discover antiinflammatory chemotherapeutics, material science, catalysis.
Microwave assisted synthesis of coumarins via potassium. Research article design and microwave assisted synthesis of coumarin derivatives as pde inhibitors mahadevn. This onepot protocol affords an effective route for the construction of functionalized coumarin structural frameworks in a single operation with moderate to high yields. Microwaveassisted synthesis, computational studies and. Microwave assisted onepot synthesis of novel trifluoromethyl coumarin thiosemicarbazones and their antifungal activities volume. Pdf coumarins appended to benzimidazole through pyrazole are designed and synthesized using microwave irradiation. Microwaveassisted synthesis of 3substituted coumarins using. Coumarins and their derivatives are very important organic compounds.
Syntheses of coumarin based dithiocarbamates have been optimized using naoh, k 3 po 4 as a base in conventional method whereas k 3 po 4 has given good yields in less time. An efficient, highyield and rapid synthesis of e1,5dimethyl42substituted2oxo2hchromen4ylmethoxynaphthalen1ylmethyleneamino2phenyl1,2dihydropyrazol3one derivatives 3a3i containing schiff base structures under microwaveirradiation has been described. Microwave assisted synthesis of 6 4methoxyphenyl 42oxo2hchromen3yl5,6 dihydropyrimidin21hone, 9d. The synthesis of novel coumarin8,7e1,3oxazine derivatives through a microwaveassisted threecomponent onepot mannich reaction is described in this study. Microwave assisted synthesis of coumarins via potassium carbonate catalyzed knoevenagel condensation in 1. Microwaveassisted organic synthesis maos has attracted attention in recent years and it is increasingly present in synthetic laboratories. Microwaveassisted synthesis of 3substituted coumarins using zrocl 2. However, previously both the knoevenagel reaction 8 and synthesis of coumarin by the knoevenagel condensation 9 have been the subject of microwave induced reactions, in the case of coumarins the only example that has been always given is the synthesis of 3ethoxycarbonylcoumarin i. Microwaveassisted synthesis of phenylpropanoids and. Microwave assisted synthesis of coumarins via potassium carbonate.
In view of our current trust in the microwaveassisted organic synthesis 47 and various. Microwave assisted synthesis of pyrazole pyrazoline. Jagadeeshprasad 3 department of chemistry, karnatak university, pavate nagar, dharwad, india. The optimized reaction conditions were also applied to the synthesis of osthol and several other natural products. Combining these features, the use of microwaveassisted processes will provide rapid access to a targeted coumarin library bearing a hydrazino pharmacophore for evaluation of antioxidant properties results microwave irradiation promoted 3 of the 4 steps in a rapid, convergent synthesis of a small library of hydrazinyl thiazolyl. Microwaveassisted heating has been used for the synthesis of coumarin derivatives. Combining these features, the use of microwaveassisted processes will provide rapid access to a targeted coumarin library bearing a. Read microwave assisted synthesis of coumarins via potassium carbonate catalyzed knoevenagel condensation in 1. Coumarins appended to benzimidazole through pyrazole are designed and synthesized using microwave irradiation. Combining these features, the use of microwaveassisted processes will provide rapid access to a targeted coumarin library bearing a hydrazino pharmacophore for evaluation of antioxidant. Microwave irradiation promoted 3 of the 4 steps in a rapid, convergent synthesis of a small library of hydrazinyl thiazolyl coumarin. The synthesis starts from an aldehyde synthon and the choice of the product, coumarin or.
If you continue browsing the site, you agree to the use of cookies on this website. In situ one pot synthesis of coumarin based dithiocarbamates have been studied under conventional and microwave methods. The use of solid acid catalysts for mw assisted synthesis of coumarin is scarce. Microwaveassisted reactions were carried out in a synthos3000. Furthermore, microwaveassisted organic synthesis has delivered rapid routes to n and ocontaining heterocycles, including coumarins and thiazoles. In microwave assisted synthesis, the mixture of 3 with various arylhetero aromatic aldehydes is irradiated in an unmodified domestic microwave oven 800w at 10 % intensity for 23 min. Pdf design and microwave assisted synthesis of coumarin. Combining these features, the use of microwaveassisted processes will provide rapid access to a targeted coumarin library bearing a hydrazino pharmacophore for evaluation of antioxidant properties. The newly constructed 1,3dimethyl7substituted2oxo2hchromen4ylmethyl1hpurine2,63h,7hdione derivatives were evaluated for their in vitro antioxidant activity by dpph free radicalscavenging ability assay and dna cleavage by using calf thymus.
Microwaveassisted synthesis of coumarins via pechmann. Since we have been working on the microwave assisted synthesis of biscoumarins,10 we decided to monitor the. Recently, it has been used for heterocyclic synthesis increasingly. A microwaveassisted synthesis of novel nacylhydrazone and semicacarbazone7hidroxycoumarins derivatives, starting from 3acetyl7hydroxy2hchromen2one, is described. Microwave irradiation has gained popularity in the past decade as a powerful. Microwaveassisted synthesis of coumarin based 1,3,5triazinyl piperazines and piperidines and their antimicrobial activities divyesh patel1, rahul patel1, premlata kumari1 and navin patel2 1applied chemistry department, s. The chosen reaction conditions determine whether a cinnamic acid or coumarin derivative is produced. Microwaveassisted coppercatalyzed fourcomponent tandem synthesis of 3nsulfonylamidine coumarins has been accomplished by the coupling of salicylaldehydes, propiolates, sulfonyl azides, and secondary amines. Journal of chemical and pharmaceutical research, 2012, 41.
Coumarin analogues are a group of bioactive molecules, found extensively in nature with a wide range of structural modifications. Combining these features, the use of microwaveassisted processes will provide rapid access to a targeted coumarin library bearing a hydrazino pharmacophore for evaluation of antioxidant properties results. The microwaveassisted synthesis is very attractive for chemical applications and has become a widely accepted nonconventional energy source for the preparation of novel heterocyclic compounds. College of sciences, henan agricultural university, zhengzhou 450002, p. Design and microwave assisted synthesis of coumarin derivatives as pde. Comparative study of the synthesis of 7 hydroxy4methyl. Microwaveassisted synthesis and photophysical studies of. Microwave assisted procedure for the preparation of compounds 5ax. A mixture of 32oxo2hchromen3yl1phenyl1hpyrazole4carbaldehyde 3ad, 1 mmol and ophenylenediamine 4af, 1 mmol taken in ethanol 5 ml was introduced into a cem microwave reaction vessel equipped with magnetic stirrer. Uv monitoring of microwave assisted biscoumarin synthesis. The application of sonochemistry for the synthesis of different coumarins from active methylene compounds and 2hydroxybenzaldehydes or resorcinol was very effective on a multigram scale with a higher yield, higher amount of crystalline compound, and shorter reaction time compared with the compounds obtained using the classical procedures. The coumarins synthesis pechmann reactionfrom by assisted microwave all reaction conditions show in tabel2 6 the coumarins synthesis from pechmann condensation by fef 3 catalyzed by assisted microwave the 1 mmol resorsinol and 1 mmol ethyl acetoacetate and 0. Guoyu yang, cuilian xu, mingqin zhao, caixia wang, sufang fan, puhui xie and xin li affiliation. Microwave assisted synthesis of some new coumarin pyrazoline hybrids and their antimicrobial activity article pdf available in journal of the serbian chemical society 803.
All the target compounds were evaluated in vitro for their antifungal activity against botrytis cinerea, colletotrichum capsici, alternaria solani, gibberella zeae, rhizoctonia solani, and alternaria mali. Based on the manual motility assessment, we observed that compounds 5d, 5f, 5g. Pdf microwave assisted convenient onepot synthesis of. Herein we describe a onepot microwaveassisted synthesis of cinnamic acid derivatives and coumarins. Coumarins be bound their class name to coumarou the vernacular name of the tonka bean dipteryx. We decided to study the microwaveassisted cadogan reaction for the synthesis of indolo3,2ccoumarins 7, as it was reported earlier that the use of the microwaveassisted technique was effective for various substrates. Coumarins are plant flavonoids widely distributed in nature. Molecules free fulltext microwave assisted synthesis. Microwaveassisted synthesis of 3substituted coumarins using zrocl2. Another one is microwave assisted convenient onepot synthesis of coumarin derivatives via pechmann condensation catalyzed by fef3 under solventfree. The rates of product formation have been monitored as a function of time. Microwaveassisted synthesis of 3substituted coumarins. Microwave assisted organic synthesis slideshare uses cookies to improve functionality and performance, and to provide you with relevant advertising.
An easy and efficient microwaveassisted protocol has been developed for the synthesis of coumarinpurine hybrids 3a3j. Alzaydi department of chemistry, girls college of education, jeddah. Coumarin, microwave synthesis, pharmacological activities, sar, various synthesis. Pdf a rapid and efficient solventfree onepot synthesis of coumarin derivatives by pechmann condensation reactions of phenols with ethyl acetoacetate. Microwave assisted synthesis of coumarinpurine derivatives. An approach to in vitro antioxidant, dna cleavage, crystal structure, dft studies and hirshfeld.
A microwaveassisted facile synthesis of novel coumarin derivatives. Microwaveassisted synthesis of fluorinated coumarino. A comparative study on catalytic activity of solid acid. Research article design and microwave assisted synthesis. Microwave assisted organic synthesis linkedin slideshare. Combining these features, the use of microwaveassisted processes will provide rapid access to a targeted coumarin library. The synthesis of coumarins and their derivatives has. A convenient approach to the design and synthesis of. Phosphoric acid imidazolium dihydrogenphosphate was found to work well as a catalyst and excellent reaction medium in the pechmann condensation of. Coumarins appended to benzimidazole through pyrazole are designed and. The synthesis begins with an aldehyde synthon, and the chosen reaction conditions determine whether a cinnamic acid or coumarin derivative is formed. National institute of technology, surat395007, india. An e cient route for the synthesis of 3substituted coumarins via knoevenagel condensation, using zrocl2.
This optimized protocol led to higher yields and considerable reduction in reaction. An efficient route for the synthesis of 3substituted coumarins via knoevenagel condensation using zrocl 2. The newly constructed 1,3dimethyl7substituted2oxo2hchromen4ylmethyl1hpurine2,63h,7hdione derivatives were evaluated for. Optimal reaction time for the synthesis was 23 min. Page 183 general papers arkivoc 2008 ii 183189 microwaveassisted synthesis of fluorinated coumarino sulfonamides hua zuo,a,c geo jose,b zhubo li,c buhyun moon,d dongsoo shin,a and manjunath ghateb adepartment of chemistry, changwon national university, changwon, korea, 641773 bdepartment of pharmaceutical chemistry, krupanidhi college of pharmacy, koramangala bangalore. Design and microwave assisted synthesis of coumarin.
Kamble, 1 sujithrajsalian, 2 sandhyakumari, 2 ramyanair, 2 guruprasadkalthur, 2 satishkumaradiga, 2 andd. Rapid solventless synthesis of 3substituted coumarins and benzocoumarins by microwave irradiation. The use of microwave mw irradiation has been employed for a number of organic transformations to reduce the reaction time, rate enhancement and to increase selectivity and yields. Microwaveassisted synthesis and antifungal activity of. The second step in the synthesis of indolo3,2ccoumarins was reductive cyclization of compounds 6. Carbonate catalyzed knoevenagel condensation in 1nbutyl3 methylimidazolium bromide ionic. The journal covers microwaveassisted synthesis of novel organic, organometallic and inorganic molecules or complexes, kinetics and mechanistic studies of. Some of the synthesized compounds, namely, 5d, 5e, 5f, 5g, 5h, and 5k, have exhibited potent inhibitory activity on pde.
Microwaveassisted synthesis of some new coumarinpyrazoline hybrids and their antimicrobial activity. Rapid solventless synthesis of 3substituted coumarins and benzocoumarins by microwave irradiation of the corresponding enaminones. Preparation methods and physical data of synthesized compounds. During the synthesis of these compounds ortho institution, panki received coumarins are classified as a member of the benzopyrone family.
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