Solvent-Free Synthesis of 5-Alkenyl-2,2-butylidene-1, 3-dioxane-4,6-diones under Ultrasonic Irradiation with o-Phthalimide-N-Sulfonic Acid as Catalyst
ABSTRACT
5-Alkenyl-2,2-butylidene-1,3-dioxane-4,6-diones were synthesized by the Knoevenagel condensation reaction of aromatic aldehydes with 2,2-butylidene-1,3-dioxane-4,6-dione using o-phthalimide-N-sulfonic acid as catalyst, without solvent under ultrasonic irradiation. The present method has some notable advantages such as mild reaction conditions, short reaction times, less catalyst dosage and high yields with the green aspects by avoiding toxic catalysts and solvents. Further, the catalyst can be reused for five times without any noticeable decrease in the catalytic activity.
KEYWORDS
o-Phthalimide-N-Sulfonicacid; 5-Alkenyl-2, 2-butylidene-1, 3-dioxane-4, 6-diones; Aromatic Aldehydes; Knoevenagel Condensation
o-Phthalimide-N-Sulfonicacid; 5-Alkenyl-2, 2-butylidene-1, 3-dioxane-4, 6-diones; Aromatic Aldehydes; Knoevenagel Condensation
Cite this paper
C. Lin, Z. Xu and W. Liao, "Solvent-Free Synthesis of 5-Alkenyl-2,2-butylidene-1, 3-dioxane-4,6-diones under Ultrasonic Irradiation with o-Phthalimide-N-Sulfonic Acid as Catalyst," International Journal of Organic Chemistry, Vol. 3 No. 4, 2013, pp. 275-279. doi: 10.4236/ijoc.2013.34039.
C. Lin, Z. Xu and W. Liao, "Solvent-Free Synthesis of 5-Alkenyl-2,2-butylidene-1, 3-dioxane-4,6-diones under Ultrasonic Irradiation with o-Phthalimide-N-Sulfonic Acid as Catalyst," International Journal of Organic Chemistry, Vol. 3 No. 4, 2013, pp. 275-279. doi: 10.4236/ijoc.2013.34039.
References
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http://dx.doi.org/10.1021/jo9520203 [22] M. M. Mojtahedi, M. S. Abaee, M. Samianifard, A. Shamloo, M. Padyab, A. W. Mesbah and K. Harms, “Ultrasound Mediation for Efficient Synthesis of Monoarylidene Derivatives of Homoand Heterocyclic Ketones,” Ultrasonics Sonochemistry, Vol. 20, No. 3, 2013, pp. 924-930.
http://dx.doi.org/10.1016/j.ultsonch.2012.11.004 [23] A. Lahyani, M. Chtourou, M. H. Frikha and M. Trabels, “Amberlyst-15 and Amberlite-200C: Efficient Catalysts for Aldol and Cross-Aldol Condensation under Ultrasound Irradiation,” Ultrasonics Sonochemistry, Vol. 20, No. 5, 2013, pp. 1296-1303.
http://dx.doi.org/10.1016/j.ultsonch.2013.01.017 [24] N. Yan, B. Xiong, W. L. Liao and Z. H. Xu, “Catalytic Synthesis of 1,3-Dioxane-4,6-dione by La(OTf)3,” Chinese Journal of Organic Chemistry, Vol. 30, No. 30, 2010, pp. 1391-1394. [25] Z. H. Xu, C. H. Lin and J. H. Xia, “An Efficient Synthesis of 1,3-Dioxane-4,6-diones by Boric Acid,” Heterocyclic Letters, Vol. 3, No. 3, 2013, pp. 319-323. [26] F. P. Xu, W. F. Ding and B. L. Da, “Reactions of 2,2-Pentamethylene-1,3-dioxan-4,6-dione with Triethyl Orthoformate and Aromatic Amines,” Chinese Journal of Organic Chemistry, Vol. 11, No. 3, 1991, pp. 318-321.
[1] R. T. Acobs, A. D. Wright and F. X. Smith, “Condensation of Monosubstituted Isopropylidene Malonates with Mannich Bases,” Journal of Organic Chemistry, Vol. 47, No. 19, 1982, pp. 3769-3772.
http://dx.doi.org/10.1021/jo00140a038 [2] R. Bruns, A. Wernicke and P. Koll, “Application of the Reaction of D-Glucose with Meldrum’s Acid: Total Synthesis of the Styryl Lactones (+)-Goniofufurone and (+)-7-epi-goniofufurone,” Tetrahedron, Vol. 55, No. 32, 1999, pp. 9793-9800. [3] I. N. Nestrova, A. K. Shanazarov and A. M. Poznyak, “Improved Method of Synthesis 2,2-Dimethyl-4,6-dioxo-1,3-dioxane (Meldrum’s Acid),” Pharmaceutical Chemistry Journal, Vol. 28, No. 8, 1994, pp. 583-585.
http://dx.doi.org/10.1007/BF02219035 [4] E. M. Abdelaziz, A. C. Jhonny Azuaje, C. Ernesto, Y. C. Matilde, Y. C. Vicente and S. Eddy, “Discovery and Preliminary SAR of 5-Arylidene-2,2-dimethyl-1,3-dioxane-4, 6-diones as Platelet Aggregation Inhibitors,” Combinatorial Chemistry & High Throughput Screening, Vol. 15, No. 7, 2012, pp. 551-554.
http://dx.doi.org/10.2174/138620712801619122 [5] W. G. Rajecwarna, R. B. Labroo and L. A. Cohen, “Synthesis of 5-[(Indol-2-on-3-yl)methyl]-2,2-dimethyl-1,3-dioxane-4,6-diones and Spirocyclopropyloxindole Derivatives. Potential Aldose Reductase Inhibitors,” Journal of Organic Chemistry, Vol. 64, No. 4, 1999, pp. 1369-1371. [6] T. Watanabe, T. F. Knpfel and E. M. Carreira, “Asymmetric Conjugate Addition Reactions of Meldrum’s Acid Derived Acceptors Employing Chiral Phosphoramidite Ligands,” Organic Letters, Vol. 5, No. 25, 2003, pp. 4557-4558. http://dx.doi.org/10.1021/ol035575q [7] E. Fillion, A. M. Dumas and S. A. Hogg, “Modular, Modular Synthesis of Tetrahydrofluorenones from 5-Alkylidene Meldrum’s Acids,” The Journal of Organic Chemistry, Vol. 71, No. 26, 2006, pp. 9899-9902.
http://dx.doi.org/10.1021/jo0618876 [8] S. Rádl, J. Stach and J. Hajicek, “An Improved Synthesis of 1,1-Dimethylethyl6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate, a Key Intermediate for Atorvastatin Synthesis,” Tetrahedron Letters, Vol. 43, No. 11, 2002, pp. 2087-2090. [9] D. Davidson and S. A. Bernhard, “The Structure of Meldrum’s Supposed β-Lactonic Acid,” Journal of the American Chemical Society, Vol. 70, No. 10, 1948, pp. 3426-3428. http://dx.doi.org/10.1021/ja01190a060 [10] E. J. Corey, “The Mechanism of the Decarboxylation of α,β-and β,γ-Unsaturated Malonic Acid Derivatives and the Course of Decarboxylative Condensation Reactions in Pyridine,” Journal of the American Chemical Society, Vol. 74, 1952, pp. 5897-5905.
http://dx.doi.org/10.1021/ja01143a021 [11] G. A. Kraus and M. E. Krolski, “Synthesis of a Precursor to Quassimarin,” Journal of Organic Chemistry, Vol. 51, No. 17, 1986, pp. 3347-3450.
http://dx.doi.org/10.1021/jo00367a017 [12] P. Scuster, O. E. Polansky and F. Wessely, “Zur Kenntnis cyclischer Acylale, 6. Mitt.,” Monatshefte für Chemie, Vol. 95, 1964, pp. 53-58.
http://dx.doi.org/10.1007/BF00909251 [13] Z. H. Xu, N. Yan and W. L. Liao, “Knoevenagel Condensation Reaction of 2,2-Dimethyl-1,3-dioxane-4,6-dione and Aromatic Aldehydes by Hexamethyldisilazane,” Chinese Journal of Jiangxi Normal University (Natural Science), Vol. 36, No. 5, 2012, pp. 524-526. [14] P. S. Rao and R. V. Venkataratnam, “Zinc Chloride as a New Catalyst for Knoevenagel Condensation,” Tetrahedron Letters, Vol. 32, No. 41, 1991, pp. 5821-5822.
http://dx.doi.org/10.1016/S0040-4039(00)93564-0 [15] A. M. Dumas and E. Fillion, “Meldrum’s Acids and 5-Alkylidene Meldrum’s Acids in Catalytic Carbon-Carbon Bond-Forming Processes,” Accounts of Chemical Research, Vol. 43, No. 3, 2009, pp. 440-454.
http://dx.doi.org/10.1021/ar900229z [16] Z. H. Xu and C. H. L, “Solvent-Free Synthesis of 5-Alkenyl-2,2-pentamethylene-1,3-dioxane-4,6-diones under Ultrasonic Irradiation with CePW12O40 as Catalyst,” Chinese Journal of Organic Chemistry, Vol. 33, No. 7, 2013, pp. 1540-1544. [17] A. M. Dumas, A. Seed, A. K. Zorzitto and E. Fillion, “A General and Practical Preparation of Alkylidene Meldrum’s Acids,” Tetrahedron Letters, Vol. 48, No. 40, 2007, pp. 7072-7074.
http://dx.doi.org/10.1016/j.tetlet.2007.08.012 [18] B. Janardhan, G. Rajitha, V. Ravibabu, B. Rajitha and A. C. Peter, “An Eco-Friendly Improved Protocol for the Synthesis of Bis(3-indolyl)methanes Using Poly(4-vinylpyridinium)hydrogen Sulfate as Efficient, Heterogeneous, and Recyclable Solid Acid Catalyst,” ISRN Organic Chemistry, Vol. 2013, 2013, pp. 1-5. [19] Z. H. Jun, J. T. Li and Y. J. Bian, “Pinacolization of Aromatic Aldehydes Using Zn/Montmorillonite K10-ZnCl2 in Aqueous THF under Ultrasound,” Chemical Journal on Internet, Vol. 5, No. 1, 2003, pp. 8-9. [20] J. T. Li, X. H. Zhang and Z. P. Lin, “An Improved Synthesis of 1,3,5-Triaryl-2-pyrazolines in Acetic Acid Aqueous Solution under Ultrasound Irradiation,” Beilstein Journal of Organic Chemistry, Vol. 13, No. 3, 2007, pp. 1-4. [21] T. P. Caulier and J. Reisse, “On Sonochemical Effects on the Diels-Alder Reaction,” Journal of Organic Chemistry, Vol. 60, No. 7, 1996, pp. 2547-2548.
http://dx.doi.org/10.1021/jo9520203 [22] M. M. Mojtahedi, M. S. Abaee, M. Samianifard, A. Shamloo, M. Padyab, A. W. Mesbah and K. Harms, “Ultrasound Mediation for Efficient Synthesis of Monoarylidene Derivatives of Homoand Heterocyclic Ketones,” Ultrasonics Sonochemistry, Vol. 20, No. 3, 2013, pp. 924-930.
http://dx.doi.org/10.1016/j.ultsonch.2012.11.004 [23] A. Lahyani, M. Chtourou, M. H. Frikha and M. Trabels, “Amberlyst-15 and Amberlite-200C: Efficient Catalysts for Aldol and Cross-Aldol Condensation under Ultrasound Irradiation,” Ultrasonics Sonochemistry, Vol. 20, No. 5, 2013, pp. 1296-1303.
http://dx.doi.org/10.1016/j.ultsonch.2013.01.017 [24] N. Yan, B. Xiong, W. L. Liao and Z. H. Xu, “Catalytic Synthesis of 1,3-Dioxane-4,6-dione by La(OTf)3,” Chinese Journal of Organic Chemistry, Vol. 30, No. 30, 2010, pp. 1391-1394. [25] Z. H. Xu, C. H. Lin and J. H. Xia, “An Efficient Synthesis of 1,3-Dioxane-4,6-diones by Boric Acid,” Heterocyclic Letters, Vol. 3, No. 3, 2013, pp. 319-323. [26] F. P. Xu, W. F. Ding and B. L. Da, “Reactions of 2,2-Pentamethylene-1,3-dioxan-4,6-dione with Triethyl Orthoformate and Aromatic Amines,” Chinese Journal of Organic Chemistry, Vol. 11, No. 3, 1991, pp. 318-321.