Green synthesis of pyran derivatives using lemon peel powder as. Reviews and accounts arkivoc 20 i 333363 page 336 arkatusa, inc. After cooling, the mixture was diluted with cold water when a solid formed which was collected by. Multicomponent synthesis of 4hpyran derivatives using koh loaded calcium oxide as catalyst in solvent free condition archana dhakara, rupendra goyalb, archana rajputa, manvendra singh kaurava, vinod s. An olefin metathesisdouble bond migration sequence of allyl ethers to cyclic enol ethers is catalyzed by first and second generation grubbs catalysts. A new insight into the stereoelectronic control of the pd0. A practical synthetic procedure for the synthesis of dihydro2hpyran34hone is reported.
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. An efficient magnetically retrievable ferritesupported glutathione nanoorganocatalyst has been employed for the synthesis of a library of 2amino4hpyran derivatives in aqueous media via a onepot multicomponent reaction. Current chemistry letters a facile and efficient protocol. The synthesis and characterization of four novel pyran derivatives 14 have been done by means of ir, 1h nmr, hrms, and single crystal xray crystallography. For example, it readily undergoes dielsalder reactions. Catalyzed synthesis of 2amino4hpyran derivatives under solventfree conditions. Compared to the previously reported procedures, these optimized conditions have significantly increased the yield of this transformation and the quality of pyran 2 and prove to be suitable for largescale preparation. The synthesis of pyran fragments 1 and 2 initiated with cglycoside 6 scheme 1, which itself was derived from trioacetyl d and lglycals according to methods previously developed in our laboratory 31. Multicomponent synthesis of 4hpyran derivatives using koh. The method commenced from the readily available ketoglutaric acid and allowed preparation of the title compound in four steps in 31% overall yield. Pdf a facile and rapid threecomponent synthesis of pharmaceutically diverse pyran annulated heterocycles has been developed via a onepot. The prepared compounds were assessed in vitro for their antimicrobial activity. Synthesis of nitrosubstituted dioxotetrahydrodioxapyrenes.
Certificate of analysis coa specification sheet pdf similar products. Sigmaaldrich offers a number of 3,4dihydro2 h pyran products. Amide derivatives of pyranone were synthesised using tbtu 21hbenzotriazol1yl1,1,3,3tetramethyluronium tetra. Synthesis of new pyran and pyranoquinoline derivatives. Methylation of 6 with meerweins reagent in the presence of proton sponge gave rise to the corresponding methyl ether in 6994% yield, which in turn was. Synthesis of pyran and pyranone natural products article pdf available in molecules 96. Further, the optical property was explored using photoluminescence spectroscopy and band gap was also calculated. Antimicrobial activities of conventional and microwave assisted synthesis of new pyran1155 h o cl 1 2 microwave irradiation cl3h c o 3 ncch2co2et pyridine ncch2cn pyridine h c o 3 nh2 o o ch3 cl. Agarwala asos in chemistry, jiwaji university, gwalior and 474011, india.
The asymmetric synthesis of a compound with the cyclopentancpyran core of iridoid natural products in four steps and 40% overall yield is reported. Our methodology includes a onepot tandem domino reaction which provides a trisubstituted cyclopentane with five new completely determined stereocenters, which were determined through 2d homo and heteronuclear nmr and n. Diastereoselective synthesis of 3,4dihydro2hpyran4. Synthesis of 3,3,4tricyano3,4dihydro2hpyran4carboxamides 2.
The synthesis of pyran fragments 1 and 2 initiated with cglycoside 6, which itself was derived from trioacetyl d and lglycals according to methods previously developed in our laboratory. Syntheses of 2hpyran2ones there are many possible ways for the synthesis of 2hpyran2ones 4, one of the more traditional ones can be retrosynthetically represented as the hydrolysis of the ester bond in the lactone ring. A 4benzyl or 4naphthylmethyl substituent is essential. The antitumor activities of the four compounds were studied in order to inhibit three human ovarian cancer cells, which are ovcar, hra and coc1, growth by mtt assay. In this study, a green, rapid and efficient protocol for the synthesis of a new series of schiff bases from spiroindoline. We report herein a new easy synthesis of this natural pyrone, using readily available starting materials. The 4hpyran derivatives are also used as photoactive materials 12 and as synthetic intermediates for dihydrofurans. Methylation of 6 with meerweins reagent in the presence of proton. Multicomponent domino reaction in the asymmetric synthesis. Microwaveassisted onepot synthesis of symmetrical 4hpyran4. Pdf synthesis of pyran annulated heterocyclic scaffolds. Synthesis of new pyran and pyranoquinoline derivatives article pdf available in arabian journal of chemistry 127s2 december 20 with 555 reads how we measure reads.
Our interest in these molecules was ignited by our need to synthesise just one member of the group in order to establish the absolute stereochemical configuration of that natural product, but has subsequently. General procedure of synthesis of pyrano2,3dpyrimidines 78 ab acetic anhydride 20 ml was added to the pyran 1 or 2 10 mmol, then orthophosphoric acid 5 ml was added carefully and the resulting hot mixture was refluxed for 3 h. Ammonium chloride catalyzed synthesis of novel schiff. The possibility of the production of nitro compounds that contain three vicinal. Design, synthesis and evaluation of new 6substituted5. In the meantime, the reuse of ionic liquids and the effect of different ionic liquids as solvent on the reaction have also been investigated. The protocol is environmentally benign and offers rapid access to a wide array of 4. The 2hpyran 2hp ring constitutes a structural motif present in many natural products. A rapid and efficient route to synthesis of 2amino4hpyran3. Over the course of this study, two key methodological advances were made. The synthesis of a range of 3hydroxy4oxo4hpyran2carboxamide with antimicrobial activity is described. General procedure for the synthesis of tetrahydrobenzobpyran and dihydro pyranocchromene derivatives in a typical reaction for the preparation of tetrahydrobenzobpyrans, an equimolar 1.
The reaction of 1,i dimethyl3,5diketocyclohexane with. Electrogenerated basepromoted synthesis of tetrahydrobenzo bpyran derivatives. Synthesis, characterization, and in vitro antimicrobial. Designing of ultrafine pdnps immobilized pyridinic. Further methodology leading potentially toward extended quinones such as 3s,3sxylindein is also outlined. Pdf synthesis of new pyran and pyranoquinoline derivatives. Sixmembered heterocyclic compounds containing oxygen such as 4hpyran4 ones. One such molecule is ib00208 1 figure 1, a polycyclic xanthone. Synthesis of pyrano3,2bpyran derivatives by condensation of kojic acid, malononitrile or ethyl cyan acetate and an aldehyde using sncl4sio2 nps as catalyst finally, a series of aromatic aldehydes were employed under similar environments to evaluate the substrate scope of this reaction. After that, raos group also designed and synthesized a series of pyran derivatives in good yields by utilizing baylishillman chemistry scheme 1c. A onepot synthesis of 3benzoylamino derivatives of 5 to 8membered cycloalkabpyran2 ones 5 and 2 h pyran2ones 10, starting from the appropriate alkanones 1 and 8, respectively, n, n dimethylformamide dimethyl acetal dmfdma and hippuric acid in the presence of a. General asymmetric synthetic strategy for the alkylated.
Synthesis of pyran and related natural products bun yeung i abstract this study was aimed at preparing dihydropyrans dhps for the synthesis of 2,6disubstituted tetrahydropyrans thps in a diastereoselective manner. Synthesis of pyran derivatives via a threecomponent condensation of. Synthesis and evaluation of antimicrobial activity of new. Synthesis of a bicyclic pyran for use as a model study in the synthesis of cytotoxic xanthone ib00208 background nature is the source of many biologically active molecules that serve as the bases for numerous drugs. The stereochemical outcome is in accord with previous observations and with the. Synthesis and biological evaluation of tetrahydrobenzob. There are two cascade mechanisms that could be proposed for. Pyran ring opening occurs and is followed by cyclization and elimination of a simple ketone which is formed from the 2 or 6substituent. Plausible reaction pathways for 3,4dihydro2hpyran4carbxamides 2 formation. Biologically active aromatic systems with appended pyran or pyranone.
Synthesis of oheterocycles synthesis of 3,4dihydro2hpyrans. Pdf synthesis of pyran and pyranone natural products. Various 2amino4hpyran3carbonitriles 1 and 2 were successfully synthesized, via a onepot threecomponent condensation reaction of arylaldehyde and. Ketoester 1 is cyclized to give pyran 3,5dione 2 in 78% yield using a parallel addition of ketoester 1 and base naotbu in refluxing thf. Kfal2o3 as an efficient and recyclable basic catalyst for. General procedure of synthesis of pyrano2,3d pyrimidines 78 ab acetic anhydride 20 ml was added to the pyran 1 or 2 10 mmol, then orthophosphoric acid 5 ml was added carefully and the resulting hot mixture was refluxed for 3 h. Article views are the countercompliant sum of full text article downloads since november 2008 both pdf and html across all institutions and individuals. The effect of the pyran ring in the benzylidene component and the length of the aliphatic radical in the aniline component on the type and thermal stability of the meso phase was ascertained. Hpyran derivatives by the reaction of aldehydes, malononitrile and active methylene dicarbonyl compounds in ethanol at room temperature is described. Unfortunately, biotechnical processes are limited by inhibition of biomass at high concentration of 6pp. A simple and green one pot protocol for the synthesis of bioactive pyran annulated heterocyclic compounds at room temperature in ethanol has.
Chemical synthesis and characterization see additional file 1 general procedure for the synthesis of compounds. Synthesis of benzothiophenefused pyran derivatives via. The aim of present study was the uses of 4 methyl cyanoacetanilide 1 in the synthesis of pyridine, pyran, thiophene, thi azole, pyrimidine, chromen derivatives together with their antitumor evaluations. Regio and stereoselective syntheses and cycloadditions of. In the present work, we are starting with cyclopentanone as the key starting material for the synthesis of pyran, pyridine, thiophene derivatives together with studying their cytotoxicity against six cancer and. A general synthetic strategy for convergent asymmetric synthesis of c1c10 fragment of tetraene. Synthesis and investigation of the mesomorphic properties. Pd complex, the pyramidalization of which confirmed by quantum chemistry calculations offers a favorable antiperiplanar alignment of the pd. Fragmentbased domain shuffling approach for the synthesis. Methods for the synthesis of tri and tetranitrosubstituted 5,9dioxo4,5,9,10tetrahydro4,10dioxapyrenes, 5,10dioxo4,5,9,10tetrahydro4,9dioxapyrenes, and 6hdibenzob,dpyran6one were developed in a search for effective sensitizers for electrophotographic layers based on carbazolecontaining polymers.
These metrics are regularly updated to reflect usage leading up to the last few days. Pdf synthesis of pyran, pyridine, thiophene, pyrimidine and. The highlight of this protocol lies in its operational simplicity, use of greener solvent, high yield within a very short period of time and reusability of the catalyst. Key steps include evans aldol reaction, hwe olefination, iodine. Synthesis of pyran, pyridine, thiophene, pyrimidine and thiazole derivatives with antitumor activities. It is isomeric with 4pyrone 2pyrone is used in organic synthesis as a building block for more complex chemical structures because it may participate in a variety of cycloaddition reactions to form bicyclic lactones. Subsequently, takakis research group was given an efficient synthetic strategy for 2amino4hchromenes from photochemical generated oquinone methides and malononitrile scheme 1b. The second step of the process, the tmsotfpromoted annulation of such silanes with the second aldehyde r 2 cho, was found to occur rapidly generally within 15 min at. Conventional and microwave assisted synthesis of new. Conclusion in conclusion, this work reports the synthesis of 2amino4h pyran3carbonitriles 1 and 2, via the simple and useful one pot three component reaction of arylaldehyde, malononitrile and methylacetoacetate or 8hydroxyquinole. After cooling, the mixture was diluted with cold water when a solid formed which was collected by filtration, washed several times with cold water and crystallization from ethanol. Pdf synthesis of pyran, pyridine, thiophene, pyrimidine.
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