Abstract
Aims and Objective: In this work, pyran derivatives were synthesized via a multicomponent reaction of ninhydrin, α-haloketones, dialkyl acetylenedicarboxylate, and triphenylphosphine in the presence of iron oxide magnetic nanoparticles (Fe3O4-MNPs) as efficient nanocatalyst in ethanol at room temperature.
Materials and Methods: The biosynthesis of Fe3O4-MNPs was performed by Clover Leaf water extract. In addition, antioxidant activity was examined for the prepared compounds employing DPPH radical scavenging and ferric reduction activity potential (FRAP) experiment and comparing results with synthetic antioxidants (TBHQ and BHT).
Results: Compound 5b showed excellent radical trapping activity and good reducing activity relative to standards (BHT and TBHQ).
Conclusion: Some advantages of this procedure are: the workup of reaction is easy and the products can be separated easily by filtration. Fe3O4-MNPs display a good improvement in the yield of the product and showed significant reusable activity.
Keywords: Ninhydrine, Fe3O4-MNPs, α-haloketones, green synthesis, Pyran, Diels-Alder reactions.
[http://dx.doi.org/10.1016/j.cclet.2015.06.014]
b) Fringuelli, F.; Taticchi, A. The Diels–Alder Reaction. Selected Practical Methods; John Wiley: New York, 2002.
c) Cycloaddition Reactions in Organic SynthesisKobayashi, S.; Jorgensen, K.A., Eds.; ; Wiley-VCH, 2002.
b) Nicolaou, K.C.; Snyder, S.A.; Montagnon, T.; Vassilikogiannakis, G. The Diels--Alder reaction in total synthesis. Angew. Chem. Int. Ed. Engl., 2002, 41(10), 1668-1698.
[http://dx.doi.org/10.1002/1521-3773(20020517)41:10<1668:AID-ANIE1668>3.0.CO;2-Z] [PMID: 19750686]
c) Corey, E.J. Catalytic enantioselective Diels--Alder reactions: methods, mechanistic fundamentals, pathways, and applications. Angew. Chem. Int. Ed. Engl., 2002, 41(10), 1650-1667.
[http://dx.doi.org/10.1002/1521-3773(20020517)41:10<1650:AID-ANIE1650>3.0.CO;2-B] [PMID: 19750685]
[http://dx.doi.org/10.1007/BFb0119240]
b) Boger, D.L.; Weinreb, S.M. Hetero Diels-Alder Methodology in Organic Synthesis; Wasserman, H.H., Ed.; Academic Press: San Diego, CA, 1987, Vol. 47, pp. 1-349.
[http://dx.doi.org/10.1021/ar00128a004]
b) Danishefsky, S.J.; DeNinno, M.P. Totally synthetic routes to the higher monosaccharides. Angew. Chem. Int. Ed. Engl., 1987, 26, 155.
[http://dx.doi.org/10.1002/anie.198700151]
c) Kametani, T.; Hibino, S. The synthesis of natural heterocyclic products by hetero Diels-Alder cycloaddition reactions. Adv. Heterocycl. Chem., 1987, 42, 245.
[http://dx.doi.org/10.1016/S0065-2725(08)60645-5]
d) Bednarski, M.D.; Lyssikatos, J.P. Comprehensive Organic Synthesis; Trost, B.M.; Heathcock, C.H., Eds.; Pergamon Press: New York, 1991, Vol. 2, p. 661.
[http://dx.doi.org/10.1016/B978-0-08-052349-1.00044-5]
[http://dx.doi.org/10.1021/ja053945v] [PMID: 16144421]
[http://dx.doi.org/10.1021/ja0648108] [PMID: 17031933]
[http://dx.doi.org/10.4236/ijoc.2012.24047]
[http://dx.doi.org/10.1021/jf052792s] [PMID: 16536586]
[http://dx.doi.org/10.1016/j.bmcl.2011.04.003] [PMID: 21515044]
[http://dx.doi.org/10.2174/1386207043328544] [PMID: 15320713]
[http://dx.doi.org/10.1246/bcsj.20120209]
[http://dx.doi.org/10.1016/0223-5234(93)90020-F]
[http://dx.doi.org/10.1002/jccs.200800098]
[http://dx.doi.org/10.1039/C39880001202]
[http://dx.doi.org/10.1016/0040-4020(96)00879-4]
[http://dx.doi.org/10.1039/JS8682100181]
[http://dx.doi.org/10.1016/S0014-827X(02)01263-6] [PMID: 12385521]
[http://dx.doi.org/10.1016/0040-4020(96)00879-4]
[http://dx.doi.org/10.1016/j.tetlet.2005.08.159]
[http://dx.doi.org/10.1007/s00706-012-0781-x] [PMID: 26166870]
[http://dx.doi.org/10.1007/s11172-005-0128-4]
[http://dx.doi.org/10.1016/j.molcata.2013.04.002]
[http://dx.doi.org/10.1016/j.matlet.2014.05.033]
[http://dx.doi.org/10.1016/j.proeng.2011.12.498]
[http://dx.doi.org/10.1039/C6RA04903F]
[http://dx.doi.org/10.1186/s11671-016-1498-2] [PMID: 27251326]
[http://dx.doi.org/10.1080/10715769900300841] [PMID: 10517532]
b) Ahmadi, F.; Kadivar, M.; Shahedi, M. Antioxidant activity of Kelussia odoratissima Mozaff. in model and food systems. Food Chem., 2007, 105, 57.
[http://dx.doi.org/10.1016/j.foodchem.2007.03.056]
[http://dx.doi.org/10.2165/00126839-200405030-00001] [PMID: 15139774]
[http://dx.doi.org/10.1301/00296640260385810] [PMID: 12462519]
[http://dx.doi.org/10.1016/j.cclet.2013.03.003]
[http://dx.doi.org/10.1007/s11030-011-9322-5] [PMID: 21695452]
[http://dx.doi.org/10.1016/j.cclet.2013.09.016]
[http://dx.doi.org/10.1080/10426507.2010.515953]
[http://dx.doi.org/10.1002/hc.21362]
[http://dx.doi.org/10.1002/jhet.2789]
[http://dx.doi.org/10.1007/s10593-017-2077-x]
[http://dx.doi.org/10.2174/1386207319666160709191851] [PMID: 27396916]
[http://dx.doi.org/10.2174/1386207318666150525094109] [PMID: 26004051]
[http://dx.doi.org/10.1021/jf00018a005]
[http://dx.doi.org/10.1021/jf00039a005]
[http://dx.doi.org/10.1007/s00706-015-1440-9]
[http://dx.doi.org/10.1007/s11947-009-0196-9]
[http://dx.doi.org/10.1021/jf0103572] [PMID: 11513714]