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Microwave Assisted Urea-Acetic Acid Catalyzed Knoevenagel Condensation of Ethyl Cyanoacetate and 1,3-Thiazolidine-2,4-dione with Aromatic Aldehydes under Solvent Free Condition

https://doi.org/10.14233/ajchem.2017.20695
Pravin T. Tryambake
Department of Chemistry, S.N. Arts, D.J.M. Commerce and B.N.S. Science College, Sangamner-422 605, India

Corresponding Author(s) : Pravin T. Tryambake

pravintryambake21@rediffmail.com

Asian Journal of Chemistry, Vol. 29 No. 11 (2017): Vol 29 Issue 11

Abstract

Knoevengel condensation reaction of various aromatic aldehydes with ethyl cyanoacetate and 1,3-thiazolidinone-2,4-diones catalyzed by urea-acetic acid under solvent free condition where olefinic products were obtained in high yield within short reaction time.

Keywords

Knoevengel condensation Solvent free Urea-Acetic acid
Tryambake, P. T. (2017). Microwave Assisted Urea-Acetic Acid Catalyzed Knoevenagel Condensation of Ethyl Cyanoacetate and 1,3-Thiazolidine-2,4-dione with Aromatic Aldehydes under Solvent Free Condition. Asian Journal of Chemistry, 29(11), 2401–2405. https://doi.org/10.14233/ajchem.2017.20695
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References
  1. G. Jones, Organic Reactions, John Wiley & Sons: New York, vol. 15, p. 204 (1967).
  2. (a) R. Ottanà, R. Maccari, M.L. Barreca, G. Bruno, A. Rotondo, A. Rossi, G. Chiricosta, R. Di Paola, L. Sautebin, S. Cuzzocrea and M.G. Vigorita, Bioorg. Med. Chem., 13, 4243 (2005); https://doi.org/10.1016/j.bmc.2005.04.058. (b) D.A. Heerding, L.T. Christmann, T.J. Clark, D.J. Holmes, S.F. Rittenhouse, D.T. Takata and J.W. Venslavsky, Bioorg. Med. Chem. Lett., 13, 3771 (2003); https://doi.org/10.1016/j.bmcl.2003.07.010. (c) A.A. Elbarbary, A.I. Khodair, E.B. Pedersen and C. Nielsen, Monatsh. Chem., 125, 593 (1994); https://doi.org/10.1007/BF00811853. (d) P. Vicini, A. Geronikaki, K. Anastasia, M. Incerti and F. Zani, Bioorg. Med. Chem., 14, 3859 (2006); https://doi.org/10.1016/j.bmc.2006.01.043. (e) H.-L. Liu, Z. Lieberzeit and T. Anthonsen, Molecules, 5, 1055 (2000); https://doi.org/10.3390/50901055. (f) R. Maccari, R. Ottanà, R. Ciurleo, M.G. Vigorita, D. Rakowitz, T. Steindl and T. Langer, Bioorg. Med. Chem., 17, 3886 (2007); https://doi.org/10.1016/j.bmcl.2007.04.109. (g) R.H. Mourão, T.G. Silva, A.L.M. Soares, E.S. Vieira, J.N. Santos, M.C.A. Lima, V.L.M. Lima, S.L. Galdino, J. Barbe and I.R. Pitta, Eur. J. Med. Chem., 40, 1129 (2005); https://doi.org/10.1016/j.ejmech.2005.06.002. (h) V.J. Ram, Drugs Today (Barc), 39, 609 (2003); https://doi.org/10.1358/dot.2003.39.8.799408. (i) J.M. Lehmann, L.B. Moore, T.A. Smith-Oliver, W.O. Wilkison, T.M. Willson and S.A. Kliewer, J. Biol. Chem., 270, 12953 (1995); https://doi.org/10.1074/jbc.270.22.12953. (j) K.G. Lambe and J.D. Tugwood, Eur. J. Biochem., 239, 1 (1996); https://doi.org/10.1111/j.1432-1033.1996.0001u.x. (k) J. Berger, P. Bailey, C. Biswas, C.A. Cullinan, T.W. Doebber, N.S. Hayes, R. Saperstein, R.G. Smith and M.D. Leibowitz, Endocrinology, 137, 4189 (1996); https://doi.org/10.1210/endo.137.10.8828476.
  3. Q.L. Wang, Y.D. Ma and B.J. Zuo, Synth. Commun., 27, 4107 (1997); https://doi.org/10.1080/00397919708005458.
  4. J.A. Cabello, J.M. Campelo, A. Garcia, D. Luna and J.M. Marinas, J. Org. Chem., 49, 5195 (1984); https://doi.org/10.1021/jo00200a036.
  5. A.V. Narsaiah and K. Nagaiah, Synth. Commun., 33, 3825 (2003); https://doi.org/10.1081/SCC-120025194.
  6. Y.M. Ren and C. Cai, Synth. Commun., 37, 2209 (2007); https://doi.org/10.1080/00397910701397375.
  7. S. Wang, Z. Ren, W. Cao and W. Tong, Synth. Commun., 31, 673 (2001); https://doi.org/10.1081/SCC-100103255.
  8. L. Rong, X. Li, H. Wang, D. Shi, S. Tu and Q. Zhuang, Synth. Commun., 36, 2407 (2006); https://doi.org/10.1080/00397910600640289.
  9. S. Balalaie and N. Nemati, Synth. Commun., 30, 869 (2000); https://doi.org/10.1080/00397910008087099.
  10. H.A. Oskooie, M.M. Heravi, F. Derikvand, M. Khorasani and F.F. Bamoharram, Synth. Commun., 36, 2819 (2006); https://doi.org/10.1080/00397910600770631.
  11. K. Mogilaiah, M. Prashanthi, G.R. Reddy, C.S. Reddy and N. Vasudeva Reddy, Synth. Commun., 33, 2309 (2003); https://doi.org/10.1081/SCC-120021512.
  12. M.S. Abaee, M.M. Mojtahedi, M.M. Zahedi and G. Khanalizadeh, ARKIVOC, 48 (2006); https://doi.org/10.3998/ark.5550190.0007.f06.
  13. W. Lehnert, Tetrahedron Lett., 54, 4723 (1970); https://doi.org/10.1016/S0040-4039(00)89377-6.
  14. H. Moison, F. Texier-Boullet and A. Foucaud, Tetrahedron, 43, 537 (1987); https://doi.org/10.1016/S0040-4020(01)89986-5.
  15. P. Shanthan Rao and R.V. Venkataratnam, Tetrahedron Lett., 32, 5821 (1991); https://doi.org/10.1016/S0040-4039(00)93564-0.
  16. B.N. Borse, S.R. Shukla and Y.A. Sonawane, Synth. Commun., 42, 412 (2012); https://doi.org/10.1080/00397911.2010.525334.
  17. M.A. Ibrahim, M.A.-M. Abdel-Hamed and N.M. El-Gohary, J. Braz. Chem. Soc., 22, 1130 (2011); https://doi.org/10.1590/S0103-50532011000600019.
  18. X.F. Li, Y.Q. Feng, W.H. Zhang and D.H. Wang, Transac. Tianjin Univ., 9, 228 (2003).
  19. (a) L.V. Sonawane and S.B. Bari, Int. J. Biol. Chem., 5, 68 (2011); https://doi.org/10.3923/ijbc.2011.68.74. (b) B.C.C. Cantello, M.A. Cawthorne, G.P. Cottam, P.T. Duff, D. Haigh, R.M. Hindley, C.A. Lister, S.A. Smith and P.L. Thurlby, J. Med. Chem., 37, 3977 (1994); https://doi.org/10.1021/jm00049a017.
  20. S. Mahalle, D. Ligampalle and R. Mane, Heteroatom Chem., 20, 151 (2009); https://doi.org/10.1002/hc.20528.
  21. M.M. Chowdhry, D.M.P. Mingos, A.J.P. White and D.J. Williams, J. Chem. Soc., Perkin Trans. 1, 20, 3495 (2000); https://doi.org/10.1039/b004312p.
  22. N.H. Metwally, N.M. Rateb and H.F. Zohdi, Green Chem. Lett. Rev., 4, 225 (2011); https://doi.org/10.1080/17518253.2010.544330.
  23. K.F. Shelke, S.B. Sapkal, G.K. Kakade, S.A. Sadaphal, B.B. Shingate and M.S. Shingare, Green Chem. Lett. Rev., 3, 17 (2010); https://doi.org/10.1080/17518250903478345.
  24. U.R. Pratap, D.V. Jawale, R.A. Waghmare, D.L. Lingampalle and R.A. Mane, New J. Chem., 35, 49 (2011); https://doi.org/10.1039/C0NJ00691B.
  25. D.H. Yang, B.Y. Yang, Z.C. Chen and S.Y. Chen, Org. Prep. Proced. Int., 38, 81 (2006); https://doi.org/10.1080/00304940609355982.
  26. B.Y. Yang and D.H. Yang, J. Chem. Res., 35, 238 (2011); https://doi.org/10.3184/174751911X13025104502362.
  27. S.R. Mahalle, P.D. Netankar, S.P. Bondge and R.A. Mane, Green Chem. Lett. Rev., 1, 103 (2008); https://doi.org/10.1080/17518250802139881.
  28. Y. Zhang and A. Zhou, Org. Chem. Int., Article ID 194784 (2012); https://doi.org/10.1155/2012/194784.
  29. K.F. Shelke, S.B. Sapkal, B.R. Madje, B.B. Shingate and M.S. Shingare, Bull. Catal. Soc. India, 8, 30 (2009).
  30. D.V. Jawale, U.R. Pratap, D.L. Lingampalle and R.A. Mane, Chin. J. Chem., 29, 942 (2011); https://doi.org/10.1002/cjoc.201190192
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