Potassium Carbonate Assisted Synthesis Of α, β, γ, δ-Unsaturated Ketones
DOI:
https://doi.org/10.17721/fujcV8I2P17-25Keywords:
Potassium carbonate, Unsaturated ketones, Claisen-Schmidt reaction, Condensation, EthanolAbstract
The Cinnamylideneacetophenones derivative is shows important medicinal properties and intermediate in organic synthesis. Several substituted α, β, γ, δ-Unsaturated Ketones were prepared in high yield and purity by direct reaction of substituted cinnamaldehyde and ketones in the presence of potassium carbonate as a base in ethanol at 50ºC. The merit of the method is short reaction times, high yield, easy work-up and purification process, inexpensive and easily available catalyst.
References
Al-Bayati F, Mohammed M, . Isolation, identification, and purification of cinnamaldehyde fromCinnamomum zeylanicumbark oil. An antibacterial study. Pharmaceutical Biology 2009;47(1):61-66. https://doi.org/10.1080/13880200802430607
Adabiardakani A, Mohammad H, Kargar H. Cinnamaldehyde Schiff Base Derivatives: A Short Review World Appl. Program. 2012; 2(11): 472-476.
Polaquini C, Torrezan G, Santos V, Nazaré A, Campos D, Almeida L, Silva I, Ferreira H, Pavan F, Duque C, Regasini L, . Antibacterial and Antitubercular Activities of Cinnamylideneacetophenones. Molecules 2017;22(10):1685. https://doi.org/10.3390/molecules22101685
Corrêa R, Fenner B, Buzzi F, Filho V, Nunes R, . Antinociceptive Activity and Preliminary Structure-Activity Relationship of Chalcone-Like Compounds. Zeitschrift für Naturforschung C 2008;63(11-12):830-836. https://doi.org/10.1515/znc-2008-11-1208
Weldon D, Saulsbury M, Goh J, Rowland L, Campbell P, Robinson L, Miller C, Christian J, Amis L, Taylor N, Dill C, Davis W, Evans S, Brantley E, . One-pot synthesis of cinnamylideneacetophenones and their in vitro cytotoxicity in breast cancer cells. Bioorganic & Medicinal Chemistry Letters 2014;24(15):3381-3384. https://doi.org/10.1016/j.bmcl.2014.05.089
Engi H, Gyemant N, Lorand T, Levai A, Ocsovszki I, Molnar J Cinnamylidene ketones as potential modulators of multidrug resistance in mouse lymphoma and human colon cancer cell lines. In vivo 2006; 20:119-124.
Riveira M, Tekwani B, Labadie G, Mischne M, . Synthesis and biological activity profile of novel 2-cinnamylidene-1,3-diones related to coruscanone A: promising new antileishmanial agents. MedChemComm 2012;3(10):1294. https://doi.org/10.1039/c2md20143g
Demers J, Hageman W, Johnson S, Klaubert D, Look R, Moore J, . Selective inhibitors of protein kinase C in a model of graft-vs-host disease. Bioorganic & Medicinal Chemistry Letters 1994;4(20):2451-2456. https://doi.org/10.1016/s0960-894x(01)80408-x
Babu K, Li X, Jacob M, Zhang Q, Khan S, Ferreira D, Clark A, . Synthesis, Antifungal Activity, and Structure−Activity Relationships of Coruscanone A Analogues. Journal of Medicinal Chemistry 2006;49(26):7877-7886. https://doi.org/10.1021/jm061123i
Sashidhara K, Kumar M, Modukuri R, Srivastava R, Soni A, Srivastava K, Singh S, Saxena J, Gauniyal H, Puri S, . Antiplasmodial activity of novel keto-enamine chalcone-chloroquine based hybrid pharmacophores. Bioorganic & Medicinal Chemistry 2012;20(9):2971-2981. https://doi.org/10.1016/j.bmc.2012.03.011
Silva E, Melo T, Sousa B, Resende D, Magalhães L, Segundo M, Silva A, Domingues M, . Do cinnamylideneacetophenones have antioxidant properties and a protective effect toward the oxidation of phosphatidylcholines?. European Journal of Medicinal Chemistry 2016;121:331-337. https://doi.org/10.1016/j.ejmech.2016.05.040
Kawamata J, Inoue K, . New Second-Order Nonlinear Optical Materials with a Cutoff Wavelength of 350 nm. 3-Benzylidene-D-camphor Derivatives. Chemistry Letters 1993;22(6):921-924. https://doi.org/10.1246/cl.1993.921
Varandas P, Rocha D, Paz F, Silva E, Silva A, . One-Pot Synthesis of Isoquinuclidines via 2,6-Diaryl-1,2-dihydropyridines using (E,E)-Cinnamylideneacetophenones as Templates. Synthesis 2018;50(10):1965-1972. https://doi.org/10.1055/s-0036-1591767
Resende D, Guieu S, Oliva C, Silva A, . Synthesis of 2,6-diaryl-1,2-dihydropyridines through a 6π-electrocyclization of N-sulfonylazatrienes. Tetrahedron Letters 2014;55(48):6585-6588. https://doi.org/10.1016/j.tetlet.2014.10.034
Lévai A, Simon A, Jenei A, Kálmán G, Jekő J, Tóth G, . Synthesis of spiro-1-pyrazolines by the reaction of exocyclic α,β,γ,δ-unsaturated ketones with diazomethane. Arkivoc 2009;2009(12):161-172. https://doi.org/10.3998/ark.5550190.0010.c14
Silva A, Cavaleiro J, Elguero J, . Oxidation of 4-Alkyl-2′-Hydroxy-2-cinnamylideneacetophenones with Thallium(III) Trinitrate: A New Synthesis of (E)-3-Styrylchromones. Liebigs Annalen 1997;1997(10):2065-2068. https://doi.org/10.1002/jlac.199719971009
Mallik AK, De SK, Chattopadhyay F A convenient synthesis of 2-benzoyl-1,5-diphenylpyrroles a class of potentially biologically active compounds. Ind. J. Chem. 2004; 43B(09):2032-2034.
LÉvai A, Patonay T, Silva A, Pinto D, Cavaleiro J, . Synthesis of 3-aryl-5-styryl-2-pyrazolines by the reaction of (E,E)-cinnamylideneacetophenones with hydrazines and their oxidation into pyrazoles. Journal of Heterocyclic Chemistry 2002;39(4):751-758. https://doi.org/10.1002/jhet.5570390421
Silva A, Resende D, Oliva C, Almeida Paz F, Cavaleiro J, . Domino Multicomponent Michael-Michael-Aldol Reactions under Phase-Transfer Catalysis: Diastereoselective Synthesis of Pentasubstituted Cyclohexanes. Synlett 2009;2010(01):115-118. https://doi.org/10.1055/s-0029-1218523
S. Silva A, Pinto D, Tavares H, Cavaleiro J, Jimeno M, Elguero J, . Novel (E)- and (Z)-2-Styrylchromones from (E, E)-2′-Hydroxycinnamylideneacetophenones – Xanthones from Daylight Photooxidative Cyclization of (E)-2-Styrylchromones. European Journal of Organic Chemistry 1998;1998(9):2031-2038. https://doi.org/10.1002/(sici)1099-0690(199809)1998:9<2031::aid-ejoc2031>3.0.co;2-#
Pinto D, Silva A, Lévai A, Cavaleiro J, Patonay T, Elguero J, . Synthesis of 3-Benzoyl-4-styryl-2-pyrazolines and Their Oxidation to the Corresponding Pyrazoles. European Journal of Organic Chemistry 2000;2000(14):2593-2599. https://doi.org/10.1002/1099-0690(200007)2000:14<2593::aid-ejoc2593>3.0.co;2-y
Kidwai M, Lal M, Mishra N, Jahan A, . Potassium carbonate as a green catalyst for Markovnikov addition of azoles to vinyl acetate in PEG. Green Chemistry Letters and Reviews 2013;6(1):63-68. https://doi.org/10.1080/17518253.2012.704082
DeLucia N, Das N, Vannucci A, . Mild synthesis of silyl ethers via potassium carbonate catalyzed reactions between alcohols and hydrosilanes. Organic & Biomolecular Chemistry 2018;16(18):3415-3418. https://doi.org/10.1039/c8ob00464a
Kidwai M, Venkataramanan R, Dave B, . Potassium carbonate, a support for the green synthesis of azoles and diazines. Journal of Heterocyclic Chemistry 2002;39(5):1045-1047. https://doi.org/10.1002/jhet.5570390530
Shi M, Dai L, Shi Y, Zhao G, . Potassium Carbonate-Catalyzed Reactions of Salicylic Aldehydes with Allenic Ketones and Esters: an Effective Way to Synthesize Functionalized 2H-Chromenes. Advanced Synthesis & Catalysis 2006;348(7-8):967-972. https://doi.org/10.1002/adsc.200505496
Jorapur Y, Jeong J, Chi D. Potassium carbonate as a base for the N-alkylation of indole and pyrrole in ionic liquids. Tetrahedron Letters 2006;47(14):2435-2438. https://doi.org/10.1016/j.tetlet.2006.01.129
Valizadeh H, Gholipur H, Shockravi A, . Microwave assisted synthesis of coumarinsviapotassium carbonate catalyzed knoevenagel condensation in 1-n-butyl-3-methylimidazolium bromide ionic liquid. Journal of Heterocyclic Chemistry 2007;44(4):867-870. https://doi.org/10.1002/jhet.5570440419
Singh S, Chauhan S, . Potassium carbonate catalyzed one pot four-component synthesis of rhodanine derivatives. Tetrahedron Letters 2013;54(20):2484-2488. https://doi.org/10.1016/j.tetlet.2013.03.004
Kidwai M, Venkataramanan R, Dave B. Green Chemistry 2001;3(6):278-279. https://doi.org/10.1039/b106034c
Mondal R, Gupta A, Mallik A, . Synthesis of flavanones by use of anhydrous potassium carbonate as an inexpensive, safe, and efficient basic catalyst. Tetrahedron Letters 2011;52(39):5020-5024. https://doi.org/10.1016/j.tetlet.2011.07.072
Li J, Lin Z, Han J, Li T, . One‐Pot Synthesis of 4‐Oxo‐2‐thioxohexahydropyrimidines Catalyzed by Potassium Carbonate Under Ultrasound. Synthetic Communications 2004;34(14):2623-2631. https://doi.org/10.1081/scc-200025624
Mohammadi S, Ghazanfari D, Karimi-Jaberi Z, . An Efficient, Potassium Carbonate-Catalysed, Three-Component Reaction of Aldehydes, Malononitrile and Amidines Leading to Highly Functionalized Pyrimidines in Aqueous Media. Letters in Organic Chemistry 2020;17(4):281-286. https://doi.org/10.2174/1570178616666190401190207
DATTA B, PASHA M, . I2/K2CO3: An efficient catalyst for the synthesis of 5-aryl-2,6-dicyano-3-methylanilines. Journal of Chemical Sciences 2013;125(2):291-294. https://doi.org/10.1007/s12039-013-0375-0
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