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. Microwaveassisted organic synthesis maos has attracted attention in recent years and it is increasingly present in synthetic laboratories. Rapid solventless synthesis of 3substituted coumarins and benzocoumarins by microwave irradiation of the corresponding enaminones. An efficient, highyield and rapid synthesis of e1,5dimethyl42substituted2oxo2hchromen4ylmethoxynaphthalen1ylmethyleneamino2phenyl1,2dihydropyrazol3one derivatives 3a3i containing schiff base structures under microwaveirradiation has been described. 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. During the synthesis of these compounds ortho institution, panki received coumarins are classified as a member of the benzopyrone family. Jagadeeshprasad 3 department of chemistry, karnatak university, pavate nagar, dharwad, india. There are some useful methods to obtain coumarin derivatives. The use of solid acid catalysts for mw assisted synthesis of coumarin is scarce. Microwaveassisted synthesis and photophysical studies of.
Comparative study of the synthesis of 7 hydroxy4methyl. Microwaveassisted heating has been used for the synthesis of coumarin derivatives. Design and microwave assisted synthesis of coumarin derivatives as pde inhibitors article pdf available february 2016 with 207 reads how we measure reads. In situ one pot synthesis of coumarin based dithiocarbamates have been studied under conventional and microwave methods. A convenient approach to the design and synthesis of. Microwave irradiation promoted 3 of the 4 steps in a rapid, convergent synthesis of a small library of hydrazinyl thiazolyl coumarin. Recently, it has been used for heterocyclic synthesis increasingly. Microwave assisted synthesis of coumarinpurine derivatives.
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. 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. If you continue browsing the site, you agree to the use of cookies on this website. Coumarins and their derivatives are very important organic compounds. Microwaveassisted synthesis of 3substituted coumarins. The synthesis of coumarins and their derivatives has. 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. Microwave irradiation has gained popularity in the past decade as a powerful. Pdf microwave assisted convenient onepot synthesis of. Optimal reaction time for the synthesis was 23 min. This onepot protocol affords an effective route for the construction of functionalized coumarin structural frameworks in a single operation with moderate to high yields.
An approach to in vitro antioxidant, dna cleavage, crystal structure, dft studies and hirshfeld. Microwave assisted synthesis of coumarins via potassium carbonate. 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. 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. National institute of technology, surat395007, india. The journal covers microwaveassisted synthesis of novel organic, organometallic and inorganic molecules or complexes, kinetics and mechanistic studies of.
Schiff base is a potential target to discover antiinflammatory chemotherapeutics, material science, catalysis. 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. Pdf coumarins appended to benzimidazole through pyrazole are designed and synthesized using microwave irradiation. Since we have been working on the microwave assisted synthesis of biscoumarins,10 we decided to monitor the. Preparation methods and physical data of synthesized compounds. Pdf microwave assisted synthesis of some new coumarin.
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. An easy and efficient microwaveassisted protocol has been developed for the synthesis of coumarinpurine hybrids 3a3j. These compounds were analyzed for phosphodiesterase pde inhibition indirectly by motility pattern in human spermatozoa. Microwave assisted synthesis of pyrazole pyrazoline. An efficient route for the synthesis of 3substituted coumarins via knoevenagel condensation using zrocl 2. 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. Microwave assisted synthesis of 6 4methoxyphenyl 42oxo2hchromen3yl5,6 dihydropyrimidin21hone, 9d. Microwave assisted onepot synthesis of novel trifluoromethyl coumarin thiosemicarbazones and their antifungal activities volume.
Microwaveassisted synthesis, computational studies and. Uv monitoring of microwave assisted biscoumarin synthesis. Microwaveassisted synthesis of coumarins via pechmann. Microwaveassisted synthesis and antioxidant properties of. Rapid solventless synthesis of 3substituted coumarins and benzocoumarins by microwave irradiation. Microwaveassisted synthesis and antifungal activity of. 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. The structures of all the compounds synthesized have been supported by analytical and spectral data. A comparative study on catalytic activity of solid acid.
Another one is microwave assisted convenient onepot synthesis of coumarin derivatives via pechmann condensation catalyzed by fef3 under solventfree. Microwaveassisted synthesis of phenylpropanoids and. Coumarin analogues are a group of bioactive molecules, found extensively in nature with a wide range of structural modifications. Read microwave assisted synthesis of coumarins via potassium carbonate catalyzed knoevenagel condensation in 1. Microwave assisted synthesis of coumarins via potassium. The rates of product formation have been monitored as a function of time. The newly constructed 1,3dimethyl7substituted2oxo2hchromen4ylmethyl1hpurine2,63h,7hdione derivatives were evaluated for. Microwave assisted synthesis of coumarins via potassium carbonate catalyzed knoevenagel condensation in 1. 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. Pdf design and microwave assisted synthesis of coumarin. Coumarin, microwave synthesis, pharmacological activities, sar, various synthesis. Conventional and microwaveassisted synthesis of new. A microwaveassisted facile synthesis of novel coumarin derivatives. Combining these features, the use of microwaveassisted processes will provide rapid access to a targeted coumarin library bearing a.
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. Coumarins appended to benzimidazole through pyrazole are designed and synthesized using microwave irradiation. Some of the synthesized compounds, namely, 5d, 5e, 5f, 5g, 5h, and 5k, have exhibited potent inhibitory activity on pde. Based on the manual motility assessment, we observed that compounds 5d, 5f, 5g. In view of our current trust in the microwaveassisted organic synthesis 47 and various. Coumarins are plant flavonoids widely distributed in nature. Microwave assisted organic synthesis slideshare uses cookies to improve functionality and performance, and to provide you with relevant advertising. Furthermore, microwaveassisted organic synthesis has delivered rapid routes to n and ocontaining heterocycles, including coumarins and thiazoles. Guoyu yang, cuilian xu, mingqin zhao, caixia wang, sufang fan, puhui xie and xin li affiliation. Carbonate catalyzed knoevenagel condensation in 1nbutyl3 methylimidazolium bromide ionic. 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.
Journal of chemical and pharmaceutical research, 2012, 41. Combining these features, the use of microwaveassisted processes will provide rapid access to a targeted coumarin library. Microwave assisted synthesis of some new coumarin pyrazoline hybrids and their antimicrobial activity article pdf available in journal of the serbian chemical society 803. Alzaydi department of chemistry, girls college of education, jeddah. 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. Microwaveassisted coppercatalyzed fourcomponent tandem. Pdf microwaveassisted synthesis of coumarinbased 5,6. Design and microwave assisted synthesis of coumarin derivatives as pde. 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. Microwaveassisted synthesis of some new coumarinpyrazoline hybrids and their antimicrobial activity. Research article design and microwave assisted synthesis of coumarin derivatives as pde inhibitors mahadevn. The synthesis begins with an aldehyde synthon, and the chosen reaction conditions determine whether a cinnamic acid or coumarin derivative is formed. Microwaveassisted reactions were carried out in a synthos3000.
This optimized protocol led to higher yields and considerable reduction in reaction. 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. The optimized reaction conditions were also applied to the synthesis of osthol and several other natural products. An e cient route for the synthesis of 3substituted coumarins via knoevenagel condensation, using zrocl2. Coumarin derivatives exhibit a wide range of biological properties including promising antioxidant activity. The chosen reaction conditions determine whether a cinnamic acid or coumarin derivative is produced. 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. Coumarins be bound their class name to coumarou the vernacular name of the tonka bean dipteryx. Microwaveassisted coppercatalyzed fourcomponent tandem synthesis of 3nsulfonylamidine coumarins has been accomplished by the coupling of salicylaldehydes, propiolates, sulfonyl azides, and secondary amines. Microwaveassisted synthesis of 3substituted coumarins using. Microwave assisted procedure for the preparation of compounds 5ax. A regioselective claisen rearrangement was also efficiently incorporated. College of sciences, henan agricultural university, zhengzhou 450002, p.
Herein we describe a onepot microwaveassisted synthesis of cinnamic acid derivatives and coumarins. Design and microwave assisted synthesis of coumarin. A microwaveassisted synthesis of novel nacylhydrazone and semicacarbazone7hidroxycoumarins derivatives, starting from 3acetyl7hydroxy2hchromen2one, is described. Molecules free fulltext microwave assisted synthesis. The synthesis of novel coumarin8,7e1,3oxazine derivatives through a microwaveassisted threecomponent onepot mannich reaction is described in this study.
Kamble, 1 sujithrajsalian, 2 sandhyakumari, 2 ramyanair, 2 guruprasadkalthur, 2 satishkumaradiga, 2 andd. Coumarins appended to benzimidazole through pyrazole are designed and. Microwaveassisted synthesis of 3substituted coumarins using zrocl2. The synthesis starts from an aldehyde synthon and the choice of the product, coumarin or.
Phosphoric acid imidazolium dihydrogenphosphate was found to work well as a catalyst and excellent reaction medium in the pechmann condensation of. Pdf a rapid and efficient solventfree onepot synthesis of coumarin derivatives by pechmann condensation reactions of phenols with ethyl acetoacetate. Microwaveassisted synthesis of fluorinated coumarino. Microwave assisted organic synthesis linkedin slideshare. Microwaveassisted solvent free synthesis of hydroxy. Microwaveassisted synthesis of 3substituted coumarins using zrocl 2. The second step in the synthesis of indolo3,2ccoumarins was reductive cyclization of compounds 6. Research article design and microwave assisted synthesis.