Abstract
Aldol reaction is one of the most established reactions employed for the construction of new C–C bond with application in chemical synthesis and biochemical domains. Conventionally, aldol reaction involved the use of basic catalyst in hydroalcoholic medium or use of strong bases in toxic and flammable organic solvents. Apart from long reaction times, such conditions result in mixtures of ketols and α, β unsaturated ketones and side products from competitive side reactions along with aldol products. In recent years, considerable efforts and interest have been put for the development of catalytic methods in green context for this transformation. Though numerous variants of homogenous and heterogeneous catalysts have been examined for better results, there are environment concerns associated with catalytic aldol reaction. Increasing ecological awareness and environment-friendly reactions has prompted chemists to involve improved strategies such as micellar medium, microwave irradiation and ultrasonics as alternative routes for aldol condensation. This review summarizes and updates the research on these routes with a green perspective. Reactions performed under these methodologies with or without use of heterogeneous catalysis have been highlighted with reference to the principles of green chemistry. The protocols have been primarily complied from pedagogical journals with depiction of green component wherever possible.
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A. Ando, T. Shioiri, Enantioselective, synthesis of β-hydroxy-α-methyl aldol reaction. Tetrahedron 45, 4969–4988 (1989). https://doi.org/10.1016/S0040-4020(01)81078-4
K.C. Nicolaou, E.J. Sorensen, S.H. Cheon et al., Classics in total synthesis. VCH New York (1996). https://doi.org/10.1021/ja00201a038
R.W. Armstrong, J.M. Beau, Total synthesis of palytoxin carboxylic acid and palytoxin amide. J. Am. Chem. Soc. 111, 7530–7533 (1989). https://doi.org/10.1021/ja00201a038
R. Kshatriya, V.P. Jejurkar, S. Saha, Recent advances in the synthetic methodologies of flavones. Tetrahedron 74, 811–833 (2018). https://doi.org/10.1016/j.tet.2017.12.052
D.N. Shah, S.K. Parikh, N.M. Shah, Synthesis of flavone- and flavonol-6-carboxylic acid and related derivatives. J. Am. Chem. Soc. 77, 2223–2224 (1955). https://doi.org/10.1021/ja01613a059
S. Mandal, S. Mandal, S.K. Ghosh, A. Ghosh, R. Saha, S. Banerjee, B.A. Saha, Review on aldol reaction. Synth. Commun. 46, 1327–1342 (2016). https://doi.org/10.1080/00397911.2016.1206938
D.G. Powers, D.S. Casebier, D. Fokas, W.J. Ryan, J.R. Troth, D.L. Coffen, Automated parallel synthesis of chalcone-based screening libraries. Tetrahedron 54, 4085–4096 (1998). https://doi.org/10.1016/S0040-4020(98)00137-9
E.P. Kohler, H.M. Chadwell, Benzalacetophenone. Org. Synth. 2, 1 (1922). https://doi.org/10.15227/orgsyn.002.0001
C.S. Marvel, L.E. Coleman, G. Scott, Pyridine analogs of chalcone and their polymerization reactions. J. Org. Chem. 20, 1785–1792 (1955). https://doi.org/10.1021/jo01364a031
F. Toda, K. Tanaka, K. Hamai, Aldol condensations in the absence of solvent: acceleration of the reaction and enhancement of the stereoselectivity. J. Chem. Soc. Perkin Trans. 1, 3207–3209 (1990). https://doi.org/10.1039/P19900003207
J. March, Advanced Organic Chemistry, 4th edn. (Wiley, New York, 1992)
N. Wachter-Jurcsak, C. Radu, K. Redin, Addressing the unusual reactivity of 2-pyridinecarboxaldehyde and 2-quinolinecarboxaldehyde in base-catalyzed aldol reactions with acetophenone. Tetrahedron Lett. 39, 3903–3906 (1998). https://doi.org/10.1016/S0040-4039(98)00723-0
H.O. House, D.S. Crumrine, A.Y. Teranishi, H.D. Olmstead, Chemistry of carbanions. XXIII. Use of metal complexes to control the aldol condensation. J. Am. Chem. Soc. 95, 3310–3324 (1973). https://doi.org/10.1021/ja00791a039
O. Petrov, Y. Ivanova, M. Gerova, SOCl2/EtOH: catalytic system for synthesis of chalcones. Catal. Commun. 9, 315–316 (2008). https://doi.org/10.1016/j.catcom.2007.06.013
T. Narender, K.P. Reddy, A simple and highly efficient method for the synthesis of chalcones by using borontrifluoride-etherate. Tetrahedron Lett. 48, 3177–3180 (2007). https://doi.org/10.1016/j.tetlet.2007.03.054
R.J. Lewis Sr., Hazardous Chemical Desk Reference, 5th edn. (Wiley, New York, 2002)
M. Sugiura, Y. Ashikari, M. Nakajima, One-pot synthesis of β, β-disubstituted α, β-unsaturated carbonyl compounds. J. Org. Chem. 80, 8830–8835 (2015). https://doi.org/10.1021/acs.joc.5b01217
Z. Wang, G. Yin, J. Qin, M. Gao, L. Cao, An efficient method for the selective iodination of α, β-unsaturated ketones. Synthesis 22, 3675–3681 (2008). https://doi.org/10.1055/s-0028-1083200
B.M. Trost, C.S. Brindle, The direct catalytic asymmetric aldol reaction. Chem. Soc. Rev. 39, 1600–1632 (2010). https://doi.org/10.1039/b923537j
Anastas PT, Warner JC, Green Chem. Theory and Practice, 1998. Oxford University Press, New York. https://doi.org/10.1021/cr078380v
I.T. Horváth, P.T. Anastas, Innovations and green chem. Chem. Rev. 107, 2169–2173 (2007). https://doi.org/10.1021/cr078380v
I.D. Cosimo, Aldol Reaction-Heterogeneous. Encyclopedia of Catalysis (Wiley, Hoboken, 2010)
E. Vrbková, T. Kovářová, E. Vyskočilová, L. Červený, Heterogeneous catalysts in the aldol condensation of heptanal with cyclopentanone. Prog. React. Kinet. 45, 1–10 (2020). https://doi.org/10.1177/1468678319825713
E. Vrbková, E. Vyskočilová, L. Červený, Functionalized MCM-41 as a catalyst for the aldol condensation of 4-isopropylbenzaldehyde and propanal. React. Kinet. Mech. Catal. 114, 675–684 (2015). https://doi.org/10.1007/s11144-014-0811-2
E. Vrbková, Z. Tišler, E. Vyskočilová et al., Aldol condensation of benzaldehyde and heptanal: a comparative study of laboratory and industrially prepared Mg-Al mixed oxides. J. Chem. Technol. Biotechnol. 93, 166–173 (2018). https://doi.org/10.1002/jctb.5336
E. Vrbková, E. Vyskočilová, L. Červený, Potassium modified alumina as a catalyst for the aldol condensation of benzaldehyde with linear C3–C8 aldehydes. React. Kinet. Mech. Catal. 121, 307–316 (2017). https://doi.org/10.1007/s11144-017-1150-x
S.K. Sharma, H.A. Patel, R.V. Jasra, Synthesis of jasminaldehyde using magnesium organo silicate as a solid base catalyst. J. Mol. Catal. A Chem. 280, 61–67 (2008). https://doi.org/10.1016/j.molcata.2007.10.013
K. Mikami, Green Reaction Media in Organic Synthesis (Blackwell Publishing Ltd, Hoboken, 2005)
K. Tanaka, Solvent-Free Organic Synthesis (Wiley, Weinheim, 2004)
P.A. Grieco, Organic Synthesis in Water (Thomson Science, London, 1998), pp. 1–278
C.J. Li, Organic reactions in aqueous media with a focus on carbon-carbon bond formations: a decade updates. Chem. Rev. 105, 3095–3165 (2005). https://doi.org/10.1021/cr030009u
S. Kobayashi, I. Hachiya, The aldol reaction of silyl enol ethers with aldehydes in aqueous media. Tetrahedron Lett. 33, 1625–1628 (1992). https://doi.org/10.1016/S0040-4039(00)91691-5
Z. Zhang, Y.W. Dong, G.W. Wang, Efficient and clean aldol condensation catalyzed by sodium carbonate in water. Chem. Lett. 32, 966–967 (2003). https://doi.org/10.1246/cl.2003.966
T. Darbre, M. Miguel, Zn-Proline catalyzed direct aldol reaction in aqueous media. Chem. Commun. 9, 1090–1091 (2003). https://doi.org/10.1039/B301117H
B.A. Hathaway, An aldol condensation experiment using a number of aldehydes and ketones. J. Chem. Educ. 64, 367 (1987). https://doi.org/10.1021/ed064p367
A.M. Saeed, M.M. Mohammad, S. Forghani et al., Inexpensive and efficient organocatalyzed procedure for aqueous aldol condensations. J. Braz. Chem.. 20, 1895–1900 (2009). https://doi.org/10.1590/S0103-50532009001000018
A. Barakat, A.M. Al-Majid, A.M. Al-Ghamdi et al., Tandem Aldol-Michael reactions in aqueous diethylamine medium: a greener and efficient approach to dimedone-barbituric acid derivatives. Chem. Cent. J. 8, 1–9 (2014). https://doi.org/10.1186/1752-153X-8-9
D.J. Guerin, D. Mazeas, M.S. Musale et al., Uridine phosphorylase inhibitors: chemical modification of benzyloxybenzyl barbituric acid and its effects on UrdPase inhibition. Bioorg. Med. Chem. Lett 9, 1477–1480 (1999). https://doi.org/10.1016/s0960-894x(99)00238-3
G. Andrews, Medical Pharmacology (The CV Mosby Co, Saint Louis, 1976), pp. 243–250
W.O. Foye, Principles of Medicinal Chemistry (Lea & Febiger, Pennsylvania, 1989), pp. 143–237
L.S. Goodman, A. Gilman, The Pharmacological Basis of Therapeutics (McGraw-Hill, New Delhi, 1991), pp. 358–360
A. Nakhaei, A. Morsali, A. Davoodnia, An efficient green approach to aldol and cross-aldol condensations of ketones with aromatic aldehydes catalyzed by nanometasilica disulfuric acid in water. Russ. J. Gen. Chem. 87, 1073–1078 (2017). https://doi.org/10.1134/S1070363217050292
X. Zhang, Y. Xiong, S. Zhang, X. Ling, J. Wang, C. Chen, Aldol condensations of aldehydes and ketones catalyzed by primary amine on water. Asian J. Chem. 24, 751–755 (2012)
N. Fakhfakh, P. Cognet, M. Cabassud, Y. Lucchese, D. de Los, M. Ríos, Stoichio-kinetic modeling and optimization of chemical synthesis: application to the aldolic condensation of furfural on acetone. Chem. Eng. Process. 4, 349–362 (2008). https://doi.org/10.1016/j.cep.2007.01.015
A. Gandini, M.N. Belgacem, Furans in polymer chemistry. Prog. Polym. Sci. 22, 1203 (1997). https://doi.org/10.1016/S0079-6700(97)00004-X
I. Sádabaa, M. Ojedaa, R. Mariscal, R. Richards, M.L. Granados, Mg–Zr mixed oxides for aqueous aldol condensation of furfural with acetone: effect of preparation method and activation temperature. Catalysis 167, 77–83 (2011). https://doi.org/10.1016/j.cattod.2010.11.059
G. Rothenberg, A.P. Downie, C.L. Raston, J.L. Scott, Understanding solid/solid organic reactions. J. Am. Chem. Soc. 123, 8701–8708 (2001). https://doi.org/10.1021/ja0034388
K.M. Doxsee, J.E. Hutchiso, Green Organic Chemistry-Strategies, Tools, and Laboratory Experiments (Brooks/Cole, Pacific Grove, 2004), pp. 115–119
C.L. Raston, J.L. Scott, Chemoselective solvent free aldol condensation reaction. Green Chem. 2, 49–52 (2000). https://doi.org/10.1039/A907688C
R.D. Palleros, Solvent free synthesis of chalcones. J. Chem. Educ. 81, 1345–1347 (2004). https://doi.org/10.1021/ed081p1345
Y. Wei, R. Bakthavatchalam, Aldol addition reaction of a lithium ester enolate in the solid state. Tetrahedron Lett. 32, 1535–1538 (1991). https://doi.org/10.1016/S0040-4039(00)74265-1
S.K. Sharma, P.A. Parikh, R.V. Jasra, Solvent free aldol condensation of propanal to 2-methylpentenal using solid base catalysts. J. Mol. Catal. A Chem. 278, 135–144 (2007). https://doi.org/10.1016/j.molcata.2007.09.00
A. Kumar, Zirconium chloride catalyzed efficient synthesis of 1, 3-diaryl-2-propenones in solvent free conditions via aldol condensation. Mol. Catal. A Chem. 274, 212–216 (2007). https://doi.org/10.1016/j.molcata.2007.05.016
T.P. Robinson, T. Ehlers, R.B. Hubbard et al., Design, synthesis, and biological evaluation of angiogenesis inhibitors: aromatic enone and dienone analogues of curcumin. Bioorg. Med. Chem. Lett. 13, 115–117 (2003). https://doi.org/10.1016/S0960-894X(02)00832-6
T.P. Robinson, R.B. Hubbard, T.J. Ehlers et al., Synthesis and biological evaluation of aromatic enones related to curcumin. Bioorg. Med. Chem. 13, 4007–4013 (2005). https://doi.org/10.1016/j.bmc.2005.03.054
A.T. Dinkova-Kostova, C. Abeygunawardana, P. Talalay, Chemoprotective properties of phenylpropenoids, bis(benzylidene)cycloalkanones, and related michael reaction acceptors: correlation of potencies as phase 2 enzyme inducers and radical scavengers. J. Med. Chem. 41, 5287–5296 (1998). https://doi.org/10.1021/jm980424s
D. Cheng, S. Valente, S. Castellano et al., Novel 3,5-Bis(bromohydroxybenzylidene)piperidin-4-ones as coactivator-associated arginine methyltransferase 1 inhibitors: enzyme selectivity and cellular activity. J. Med. Chem. 54, 4928–4932 (2011). https://doi.org/10.1021/jm200453n
J.R. Dimmock, M.P. Padmanilayam, G.A. Zello et al., Cytotoxic analogues of 2,6-bis(arylidene)cyclohexanones. Eur. J. Med. Chem. 38, 169–177 (2003). https://doi.org/10.1016/S0223-5234(02)01444-7
A. Modzelewska, C. Pettit, G. Achanta, N.E. Davidson, P. Huang, S.R. Khan, Anticancer activities of novel chalcone and bis-chalcone derivatives. Bioorg. Med. Chem. 14, 3491–3495 (2006). https://doi.org/10.1016/j.bmc.2006.01.003
C. Piantadosi, I.H. Hall, J.L. Irvine, G.L. Carlson, Cycloalkanones. 2. Synthesis and biological activity of alpha, alpha’-dibenzylcycloalkanones. J. Med. Chem. 16, 770–795 (1973). https://doi.org/10.1021/jm00265a006
J. Deli, T. Lorand, D. Szabo, A. Foldesi, Potential bioactive pyrimidine derivatives, part 1: 2-Amino-4-aryl-8-arylidene-3,4,5,6,7,8 hexahydroquinazolines. Pharmazie 39, 539–540 (1984)
N.J. Leonard, L.A. Miller, J.W. Berry, The synthesis of 2,7-disubstituted tropones via aromatization. J. Am. Chem. Soc. 79, 1482–1485 (1957). https://doi.org/10.1021/ja01563a056
M.A. Ciufolini, N.E. Byrne, The total synthesis of cystodytins. J. Am. Chem. Soc. 113, 8016–8024 (1991). https://doi.org/10.1021/ja00021a031
A.F.M. Rahman, R. Ali, Y. Jahng, A.A. Kadi, A facile solvent free Claisen-Schmidt reaction: synthesis of α, α′-bis-(substituted-benzylidene)cycloalkanones and α, α′-bis-(substituted-alkylidene)cycloalkanones. Molecules 17, 571–583 (2012). https://doi.org/10.3390/molecules17010571
G.H. Mahdavinia, S. Rostamizadeh, A.M. Amani, M. Mirzazadeh, NH4H2PO4/SiO2: a recyclable, efficient heterogeneous catalyst for crossed aldol condensation reaction. Green Chem. Lett. Rev. 5(3), 255–281 (2012). https://doi.org/10.1080/17518253.2011.617317
M.S. Abaee, M.M. Mojtahedi, R. Sharifi et al., Facile synthesis of bis(arylmethylidene)cycloalkanones mediated by lithium perchlorate under solvent-free conditions. J. Iran. Chem. Soc. 3, 293–296 (2006). https://doi.org/10.1007/BF03247222
T.M. Robinson, M.C. Box, M.T.G. Williams, Choose your own (green) adventure: a solventless aldol condensation experiment for the organic chemistry laboratory. World J. Chem. Educ. 8, 104–106 (2020). https://doi.org/10.12691/wjce-8-3-1
D. Xie, Y. Xie, Y. Ding, J. Wu, D. Hu, Synthesis of chiral chalcone derivatives catalyzed by the chiral cinchona alkaloid squaramide. Molecule 19, 19491–19500 (2014). https://doi.org/10.3390/molecules191219491
C. Deepak, S. Nisha, Crossed aldol condensation (CAC) as a feasible route for synthesis of a 1, 2-unsaturated carbonyl compound-1,3 diphenylpropenone. Arch. Chem. Res. 1, 1–6 (2016). https://doi.org/10.21767/2572-4657.100002
D.S. Desai, G.D. Yadav, Green synthesis of furfural acetone by solvent-free aldol condensation of furfural with acetone over La2O3–MgO mixed oxide catalyst. Ind. Eng. Chem. Res. 58, 16096–16105 (2019). https://doi.org/10.1021/acs.iecr.9b01138
M. Nasseri, A. Allahresani, H. Raissi, A new application of nano-graphene oxide as a heterogeneous catalyst in crossed-aldol condensation reaction under solvent-free conditions. Iran. J. Catal. 4, 33–40 (2014)
T. Dwars, E. Paetzold, G. Oehme, Reactions in micellar medium. Angew. Chem. Int. Ed. 44, 7174 (2005). https://doi.org/10.1002/anie.200501365
J.H. Fendler, E.J. Fendler, Catalysis in Micellar and Macromolecular Systems (Academic Press, New York, 1975)
B.H. Lipshutz, N.A. Isley, J.C. Fennewald, E.D. Slack, On the way towards greener transition-metal-catalyzed processes as quantified by E factors. Angew. Chem. Int. Ed. 52, 10952–10958 (2013). https://doi.org/10.1002/anie.201302020
B.H. Lipshutz, “Nok”: a phytosterol-based amphiphile enabling transition-metal-catalyzed couplings in water at room temperature. J. Org. Chem. 79, 888–900 (2014). https://doi.org/10.1021/jo401744b
J.J. Shrikhande, M.B. Gawande, R.V. Jayaram, Cross-aldol and knoevenagel condensation reactions in aqueous micellar media. Catal. Commun. 9, 1010–1016 (2008). https://doi.org/10.1016/j.catcom.2007.10.001
M. Vashishtha, M. Mishra, D.O. Shah, A novel approach for selective cross aldol condensation using reusable NaOH-cationic micellar systems. Appl. Catal. A Gen. 466, 38–44 (2013). https://doi.org/10.1016/j.apcata.2013.06.015
M. Vashishtha, M. Mishra, U. Singh, O.D. Shah, Molecular mechanism of micellar catalysis of cross aldol reaction: effect of surfactant chain length and surfactant concentration. J. Mol. Catal. A Chem. 396, 143–154 (2015). https://doi.org/10.1016/j.molcata.2014.09.023
B.S. Kitawat, M. Singh, R.K. Kale, Robust cationic quaternary ammonium surfactant catalyzed condensation reaction for (E)-3-Aryl-1-(3-alkyl-2-pyrazinyl)-2-propenone synthesis in water at room temperature. ACS Sustain. Chem. Eng. 1, 1040–1044 (2013). https://doi.org/10.1021/sc400102e
A. Saito, J. Numaguchi, Y. Hanzawa, Pictet-Spengler reactions catalyzed by Brønsted acid surfactant-combined catalyst in water or aqueous media. Tetrahedron Lett. 48, 835–839 (2007). https://doi.org/10.1016/j.tetlet.2006.11.147
S. Shirakawa, S. Kobayashi, Surfactant-type Brønsted acid catalyzed dehydrative nucleophilic substitutions of alcohols in water. Org. Lett. 9, 311–314 (2007). https://doi.org/10.1021/ol062813j
K. Phatangarea, V. Padalkara, K. Muruganb, A. Chaskarb, Bronsted acid-surfactant (BAS) catalyzed cyclotrimerization of aryl methyl ketone. Curr. Chem. Lett. 1, 133–138 (2012). https://doi.org/10.5267/j.ccl.2012.5.001
A. Loupy, Microwaves in Organic Synthesis (Wiley, Weinheim, 2006)
E. Martin, C.K. Yuen, Microwave assisted organic synthesis in the organic teaching lab: a simple, greener Wittig reaction. J. Chem. Educ. 84, 2004–2006 (2007). https://doi.org/10.1021/ed084p2004
G.L. Kad, K.P. Kaur, V. Singh, J. Singh, Microwave induced rate enhancement in aldol condensation. Synth. Commun. 29, 2583–2586 (1999). https://doi.org/10.1080/00397919908086416
S. Handayani, C. Budimarwanti, W. Haryadi, Microwave-assisted organic reactions: eco-friendly synthesis of dibenzylidenecyclohexanone derivatives via crossed aldol condensation. Indones. J. Chem. 17, 336–341 (2017). https://doi.org/10.22146/ijc.25460
M. Da’i, A.M. Supardjan, E. Meiyanto, U.A. Jenie, Isomers geometric dan efek sitotoksik pada sel T47D dari analog kurkumin PGV-0 and PGV-1. Indones. J. Pharm. 18, 40–47 (2007). https://doi.org/10.14499/INDONESIANJPHARM0ISS0PP40-47
D. Limnios, C.G. Kokotos, Microwave-assisted organocatalytic cross-aldol condensation of aldehydes. RSC Adv. 14, 4496–4499 (2013). https://doi.org/10.1039/C3RA00114H
M. Ali, S. Ertürk, A. Umaz, Microwave-assisted intermolecular aldol condensation: efficient one-step synthesis of 3-acetyl isocoumarin and optimization of different reaction conditions. Arab. J. Chem. 11, 538–545 (2018). https://doi.org/10.1016/j.arabjc.2015.11.013
R. Mondal, T.K. Mandal, A.K. Mallik, An expeditious and safe synthesis of some exocyclic α, β-unsaturated ketones by microwave-assisted condensation of cyclic ketones with aromatic aldehydes over anhydrous potassium carbonate. Org. Chem. Int. (2012). https://doi.org/10.1155/2012/456097
A.S. Mamman, J.M. Lee, Y.C. Kim et al., Furfural: hemicellulose/xylosederived biochemical. Biofuels Bioprod. Biorefin. Innov. Sustain. Econ. 2, 438–454 (2008). https://doi.org/10.1002/bbb.95
R. Mariscal, P.M. Torres, M. Ojeda, I. Sádaba, M.L. Granados, Furfural: a renewable and versatile platform molecule for the synthesis of chemicals and fuels. Energy Environ. Sci. 9, 1144–1189 (2006). https://doi.org/10.1039/C5EE02666K
G.W. Huber, J.N. Chheda, C.J. Barrett, J.A. Dumesic, Production of liquid alkanes by aqueous-phase processing of biomass-derived carbohydrates. Science 308, 1446–1450 (2005). https://doi.org/10.1126/science.1111166
L. Faba, E. Díaz, S. Ordóñez, Aqueous-phase furfural-acetone aldol condensation over basic mixed oxides. Appl. Catal. B Environ. (2012). https://doi.org/10.1016/j.apcatb.2011.11.039
L. Smoláková, L. Dubnová, J. Kocík et al., In-situ characterization of the thermal treatment of Zn-Al hydrotalcites with respect to the formation of Zn/Al mixed oxide active in aldol condensation of furfural. Appl. Clay Sci. 157, 8–18 (2018). https://doi.org/10.1016/j.clay.2018.02.024
O. Kikhtyanin, P. Chlubná, T. Jindrová, D. Kubička, Peculiar behavior of MWW materials in aldol condensation of furfural and acetone. Dalton Trans. 43, 10628–10641 (2014). https://doi.org/10.1039/C4DT00184B
A. Tampieri, M. Lilic, M. Constantí, F. Medina, Microwave-assisted aldol condensation of furfural and acetone over Mg–Al hydrotalcite-based catalysts. Curr. Comput. Aided Drug Des. 10, 833 (2020). https://doi.org/10.3390/cryst10090833
S. Handayani, I.S. Arty, Synthesis of hydroxyl radical scavengers from benzalacetone and its derivatives. J. Phys. Sci. 19, 61–68 (2008)
N.L. Drake, P. Allen, Benzalacetone. J. Org. Synth. (1923). https://doi.org/10.15227/orgsyn.003.0017
A. Rayar, M.S.I. Veitía, C. Ferroud, An efficient and selective microwave-assisted Claisen-Schmidt reaction for the synthesis of functionalized benzalacetones. Springer Plus 4, 221 (2015). https://doi.org/10.1186/s40064-015-0985-8
A. Cornelis, P. Laszlo, Molding clays into efficient catalysts. Synth. Lett. 3, 155–161 (1994). https://doi.org/10.1055/S-1994-22775
J.S. Yadav, B.V.S. Reddy, G.M. Kumar, C.V.S.R. Murthy, Montmorillonite clay catalyzed in situ Prins-type cyclisation reaction. Tetrahedron Lett. 42, 89–91 (2001). https://doi.org/10.1016/S0040-4039(00)01891-8
J.S. Yadav, B.V.S. Reddy, K.S. Patil, P.S.R. Reddy, Montmorillonite clay-catalyzed [4+2] cycloaddition reactions: a facile synthesis of pyrano- and furanoquinolines. Tetrahedron Lett. 43, 3853–3856 (2002). https://doi.org/10.1016/S0040-4039(02)00679-2
A.E. Esmaeili, M.S. Tabas, A. Mohammad, N.S.F. Kazemi, Solvent-free crossed aldol condensation of cyclic ketones with aromatic aldehydes assisted by microwave irradiation. Monatshefte fur Chemie 136, 571–576 (2005). https://doi.org/10.1007/s00706-004-0256-9
S. Peddibhotla, 3-substituted-3-hydroxy-2-oxindole, an emerging new scaffold for drug discovery with potential anti-cancer and other biological activities. Curr. Bioactive Compd. 5, 20–38 (2009). https://doi.org/10.2174/157340709787580900
P. Hewawasam, M. Erway, S.L. Moon, J. Knipe et al., Synthesis and structure−activity relationships of 3-aryloxindoles: a new class of calcium-dependent, large conductance potassium (Maxi-K) channel openers with neuroprotective properties. J. Med. Chem. 45, 1487–1499 (2002). https://doi.org/10.1021/jm0101850
T. Tokunaga, W.E. Hume, T. Umezome et al., Oxindole derivatives as orally active potent growth hormone secretagogues. J. Med. Chem. 44, 4641–4649 (2001). https://doi.org/10.1021/jm0103763
Y. Koguchi, J. Kohno, M. Nishio et al., TMC-95A, B, C, and D, novel proteasome inhibitors produced by Apiospora montagnei Sacc TC 1093. Taxonomy, production, isolation, and biological activities. J. Antibiot. 53, 105–109 (2000). https://doi.org/10.7164/antibiotics.53.105
S. Nakamura, N. Hara, H. Nakashima et al., Enantioselective synthesis of (R)-convolutamydine A with new N-heteroarylsulfonylprolinamides. Chem. Eur. J. 14, 8079–8081 (2008). https://doi.org/10.1002/chem.200800981
J.R. Chen, X.P. Liu, X.Y. Li, L. Zhu, Organocatalytic asymmetric aldol reaction of ketones with isatins: straightforward stereoselective synthesis of 3-alkyl-3-hydroxyindolin-2-ones. Tetrahedron 63, 10437–10444 (2007). https://doi.org/10.1016/j.tet.2007.08.003
R. Shintani, M. Inoue, T. Hayashi, Rhodium-catalyzed asymmetric addition of aryl- and alkenylboronic acids to isatins. Angew. Chem. Int. Ed. 45, 3353–3356 (2006). https://doi.org/10.1002/anie.200600392
T. Ishimaru, N. Shibata, J. Nagai, S. Nakamura, T. Toru, S. Kanemasa, Lewis acid-catalyzed enantioselective hydroxylation reactions of oxindoles and β-keto esters using DBFOX ligand. J. Am. Chem. Soc. 128, 16488–16489 (2006). https://doi.org/10.1021/ja0668825
G. Luppi, M. Monari, R.J. Correa et al., The first total synthesis of (R)-convolutamydine A. Tetrahedron 62, 12017–12024 (2006). https://doi.org/10.1016/j.tet.2006.09.077
B.M. Trost, M.U. Frederiksen, Palladium-catalyzed asymmetric allylation of prochiral nucleophiles: synthesis of 3-allyl-3-aryl oxindoles. Angew. Chem. Int. Ed. 44, 308–310 (2005). https://doi.org/10.1002/anie.200460335
T. Kawasaki, M. Nagaoka, T. Satoh et al., Synthesis of 3-hydroxyindolin-2-one alkaloids, (±)-donaxaridine and (±)-convolutamydines A and E, through enolization–Claisen rearrangement of 2-allyloxyindolin-3-ones. Tetrahedron 60, 3493 (2004). https://doi.org/10.1016/j.tet.2004.02.031
I.D. Hills, G.C. Fu, Catalytic enantioselective synthesis of oxindoles and benzofuranones that bear a quaternary stereocenter. Angew. Chem. Int. Ed. 42, 3921–3924 (2003). https://doi.org/10.1002/anie.200351666
W.B. Chen, Y.H. Liao, X.L. Du, X.M. Zhang, W.C. Yuan, Catalyst-free aldol condensation of ketones and isatins under mild reaction conditions in DMF with molecular sieves 4 Å as additive. Green Chem. 11, 1465–1476 (2009). https://doi.org/10.1039/B906684E
H.M. Meshram, N. Nageswara Rao, N. Satish Kumar, L. Chandrasekhara Rao, Microwave assisted catalyst free synthesis of 3-hydroxy-2-oxidoles by aldol condensation of acetophenones with isatins. Der Pharma Chem. 4, 1355–1360 (2012)
R. Bakhshi, B. Zeynizadeh, H. Mousavi, Green, rapid, and highly efficient syntheses of α, α-bis[(aryl or allyl)idene]cycloalkanones and 2-[(aryl or allyl)idene]- 1-indanones as potentially biologic compounds via solvent-free microwave-assisted Claisen-Schmidt condensation catalyzed by MoCl5. J. Chin. Chem. Soc. 67, 623–637 (2020). https://doi.org/10.1002/jccs.201900081
B. Mounir, F. Bazi, A. Mounir, M. Zahouily, H. Toufik, Sodium-modified fluorapatite: a mild and efficient reusable catalyst for the synthesis of α, α’-bis(substituted benzylidene) cycloalkanones under conventional heating and microwave irradiation. Green Sustain. Chem. 8, 156–166 (2018). https://doi.org/10.4236/gsc.2018.82011
T. Welton, Room-temperature ionic liquids: solvents for synthesis and catalysis. Chem. Rev. 99, 2071–2083 (1999). https://doi.org/10.1021/cr980032t
J.P. Hallett, T. Welton, Room-temperature ionic liquids: Solvents for synthesis and catalysis. Chem. Rev. 111, 3508–3576 (2011). https://doi.org/10.1021/cr1003248
P. Wasserscheid, W. Keim, Ionic liquids: new “solutions” for transition metal catalysis. Angew. Chem. Int. Ed. 39, 3772–3789 (2000). https://doi.org/10.1002/1521-3773(20001103)39:21%3C3772::AID-ANIE3772%3E3.0.CO;2-5
A.C. Cole, J.L. Jensen, I. Ntai, K.L.T. Tran et al., Novel brønsted acidic ionic liquids and their use as dual solvent-catalysts. J. Am. Chem. Soc. 124, 5962–5963 (2002). https://doi.org/10.1021/ja026290w
B.C. Ranu, S. Banerjee, Ionic liquid as catalyst and reaction medium. The dramatic influence of a task-specific ionic liquid, [bmim] OH, in Michael addition of active methylene compounds to conjugated ketones, carboxylic esters and nitriles. Org. Lett. 7, 3049–3052 (2005). https://doi.org/10.1021/ol051004h
C.P. Mehnert, N.C. Dispenziere, R.A. Cook, Preparation of C9-aldehyde via aldol condensation reactions in ionic liquid media. Chem. Commun. (2002). https://doi.org/10.1039/B203068C
S. Hu, T. Jiang, Z. Zhang et al., Functional ionic liquid from biorenewable materials: synthesis and application as a catalyst in direct aldol reactions. Tetrahedron Lett. 48, 5613–5617 (2007). https://doi.org/10.1016/j.tetlet.2007.06.051
X. Cui, S. Zhang, F. Shi, Q. Zhang, Q.X. Ma, L. Lu, Y. Deng, The influence of the acidity of ionic liquids on catalysis. Chemsuschem 3, 1043–1047 (2010). https://doi.org/10.1002/cssc.201000075
S.K. Karmee, U. Hanefeld, Ionic liquid catalysed synthesis of β-hydroxy ketones. Chemsuschem 4, 1118–1123 (2011). https://doi.org/10.1002/cssc.201100083
S. Luo, H. Xu, J. Li et al., Facile evolution of asymmetric organocatalysts in water assisted by surfactant Brønsted acids. Tetrahedron 63, 11307–11314 (2007). https://doi.org/10.1016/j.tet.2007.08.096
S. Luo, X. Mi, L. Zhang et al., Functionalized ionic liquids catalyzed direct aldol reactions. Tetrahedron 63, 1923–1930 (2007). https://doi.org/10.1016/j.tet.2006.12.079
C. Wang, J. Liu, W. Leng, Y. Gao, Rapid and efficient functionalized ionic liquid-catalyzed aldol condensation reactions associated with microwave irradiation. Int. J. Mol. Sci. 15, 1284–1299 (2014). https://doi.org/10.3390/ijms15011284
K.S. Suslick, Mechanochemistry and sonochemistry: concluding remarks. Faraday Discuss. 170, 411–422 (2014). https://doi.org/10.1039/C4FD00148F
M.A. Margulis, Fundamental problems of sonochemistry and cavitation. Ultrason. Sonochem. 1, S87–S90 (1994). https://doi.org/10.1016/1350-4177(94)90003-5
R. Tanaka, N. Takahashi, Y. Nakamura et al., Verification of the mixing processes of the active pharmaceutical ingredient, excipient and lubricant in a pharmaceutical formulation using a resonant acoustic mixing technology. RSC Adv. 6, 87049–87057 (2016). https://doi.org/10.1016/1350-4177(94)90003-5
L.C. Hagenson, L.K. Doraiswamy, Comparison of the effects of ultrasound and mechanical agitation on a reacting solid-liquid system. Chem. Eng. Sci. 53, 131–148 (1998). https://doi.org/10.1016/S0009-2509(97)00193-0
T.J. Mason, E.D. Cordemans, Ultrasonic intensification of chemical processing and related operations: a review. Chem. Eng. Res. Des.. 74, 511–516 (1996)
B.C. Barot, D.W. Sullins, E.J. Eisenbraun, Ultrasonic agitation in basic alumina catalyzed aldol condensation of ketones. Synth. Commun. 14, 397–400 (1984). https://doi.org/10.1080/00397918408059557
J.L. Luche, Synthetic Organic Sonochemistry (Plenum Press, New York, 1998)
G. Cravotto, A. Demetri, G. Nano et al., The aldol reaction under high-intensity ultrasound: a novel approach to an old reaction. Chem. Eur. J. 22, 4438–4444 (2013). https://doi.org/10.1002/ejoc.200300369
N.G. Khaligh, T. Mihankhah, Aldol condensations of a variety of different aldehdyes and ketones under ultrasonic irradiation using poly(N-vinylimidazole) as a new heterogeneous base catalyst under solvent-free conditions in a liquid-solid system. Chin. J. Catal. 34, 2167–2173 (2013). https://doi.org/10.1016/S1872-2067(12)60658-5
D.E. Crawford, Solvent-free sonochemistry: sonochemical organic synthesis in the absence of a liquid medium. Beilstein J. Org. Chem. 13, 1850–1856 (2017). https://doi.org/10.3762/bjoc.13.179
N. Cancio, A.R. Costantino, G.F. Silbestri, M.T. Pereyra, Ultrasound-assisted syntheses of chalcones: experimental design and optimization. Proceedings 41, 1–8 (2019)
A. Lahyani, M. Chtourou, M. HédiFrikha, M. Trabelsi, Amberlyst-15 and Amberlite-200C: efficient catalysts for aldol and cross-aldol condensation under ultrasound irradiation. Ultrason. Sonochem. 20, 1296–1301 (2013). https://doi.org/10.1016/j.ultsonch.2013.01.017
K. Juvale, V.F.S. Pape, M. Wiese, Investigation of chalcones and benzochalcones as inhibitors of breast cancer resistance protein. Bioorg. Med. Chem. 20, 346 (2012). https://doi.org/10.1016/j.bmc.2011.10.074
A.A. Tri Suma, T.D. Wahyuningsih, H.S. Mustofa, Efficient synthesis of Chloro Chalcones under ultrasound irradiation, their anticancer activities and molecular docking studies. Rasayàn J. Chem. 12, 502–510 (2019). https://doi.org/10.31788/RJC.2019.1225020
M.M. Mojtahedi, L. Afshinpoor, F. Karimi et al., Green synthesis of dissymmetric bisarylidene derivatives of cyclohexanone analogues under ultrasonic conditions. J. Iran Chem. Soc. 16, 209–217 (2019). https://doi.org/10.1007/s13738-018-1498-5
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Bargujar, S., Ratnani, S. Aldol condensation: green perspectives. J IRAN CHEM SOC 19, 2171–2190 (2022). https://doi.org/10.1007/s13738-021-02464-w
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DOI: https://doi.org/10.1007/s13738-021-02464-w