Recent Scenario: Knoevenagel Condensation in Organic Synthesis: A Review

"Modern organic synthesis emphasizes sustainability, selectivity, and efficiency. Carbon-carbon bond formation is crucial in organic synthesis, and the Knoevenagel condensation reaction is one of the most powerful tools for this purpose. Green methodologies—including solvent-free conditions, water/ionic liquids, and bio-based solvents—along with metal-free or earth-abundant metal catalysis (e.g., cobalt, copper, single-atom catalysts) are increasingly preferred. This review provides a comprehensive overview of recent developments in Knoevenagel condensation, highlighting key synthetic pathways, catalytic systems, and applications."

Knoevenagel condensation, ethyl acetoacetate, Di isopropyl ethyl ammonium acetate (DIPEAc)

1. Knoevengel,E.;Chem. Ber.,1898, 31 (3), 2596. [Google Scholar] [Crossref]

2. Cope,A.C.;J.Am.Chem.Soc., 1937,59(11), 2327. [Google Scholar] [Crossref]

3. Cope,A.C.;Hoyle,K.E.;J.Am. Chem.Soc.,1941,63(3), 733. [Google Scholar] [Crossref]

4. Cope,A.C.;Hofmann,C.M.;Wyckoff,C.;Hardenberg,E.;J.Am.Chem.Soc.,1941,63(12),3452. [Google Scholar] [Crossref]

5. Lombardo, M.; Pasi, F.; Easwar, S.; Trombini, C.; Adv. Synth. Catal., 2007, 349, 2061. [Google Scholar] [Crossref]

6. Zhou, L.; Wang, L.; Chem. Lett., 2007, 36, 628. [Google Scholar] [Crossref]

7. Siyutkin, D.E.; Kucherenko, A. S.; Struchkova, M. I.; Zlotin, S. G.; Tetrahedron Lett., 2008, 49, 1212. [Google Scholar] [Crossref]

8. Ni, B.; Headley, A. D.; Chem. Eur. J., 2010, 16, 4426. [Google Scholar] [Crossref]

9. Handy, S. T.; J. Org. Chem., 2006, 71(12), 4659. [Google Scholar] [Crossref]

10. Anjaiah, S.; Chandrasekhar, S.; Gree, R.; J. Mol. Catal. A. Chem., 2004, 214, 103. [Google Scholar] [Crossref]

11. Rodionow, W. M.; J. Am. Chem. Soc., 1929, 51, 847. [Google Scholar] [Crossref]

12. Wang, Y.; Shang, Z.; Wu, T.; Fan, T.; Chen, J.; J. Mol. Catal. A. Chem., 2006, 253, 212. [Google Scholar] [Crossref]

13. Zhu, L.; Lei, N.; Miao, Z.; Sheng, C.; Zhuang, C.; Yao, J.; Zhang, W.; Chin. J. Chem., 2012, 30, 139. [Google Scholar] [Crossref]

14. Gupta, M.; Wakhloo, B. P.; ARKIVOC, 2007, 94. [Google Scholar] [Crossref]

15. Sanjoy, K.; Nimalini, M.; Warjeet, S. L.; Indian Journal of Chemistry, 2015, 54B, 1157. [Google Scholar] [Crossref]

16. Rajesh Krihnan, G. P.; Sreekumar, K.; Tetrahedron Lett. 2014, 55, 2352. [Google Scholar] [Crossref]

17. Zhang, Q.; Ma, X. M.; Wei, H. X.; Zhao, X.; Luo, J.; RSC Adv., 2017, 7, 53861. [Google Scholar] [Crossref]

18. Wan, J. P.; Jing, Y.; Liu, Y.; Sheng, S.; RSC Adv., 2014, 4, 63997. [Google Scholar] [Crossref]

19. de Paula, B. R. S.; Zampieri, D. S.; Zukerman-Schpector, J.; Tiekink, E. R. T.; Rodrigues, J. A. R.; Moran, P. J. S.; J. Braz. Chem. Soc. 2012, 23 (5), 825. [Google Scholar] [Crossref]

20. Kolahdoozan, M.; Kalbasi, R. J.; Shahzeidi, Z. S.; Zamani, F.; J. Chem., 2013, doi.org/10.1155/2013/496837. [Google Scholar] [Crossref]

21. Meng,D.;Qiao,Y.; Wang,X.; Wen,W.; Zhao,S.;RSCAdv.,2018,8, 30180. [Google Scholar] [Crossref]

22. Texiey-Boullet,F.;Foucaud,A.;TetrahedronLett.,1982,23,4927. [Google Scholar] [Crossref]

23. Lu,Y.Y.;Ren,Z.J.;Cao,W.G.;Tong,W.Q.;Gao,M.F.;Syn.Comm.,2004,34,2047. [Google Scholar] [Crossref]

24. Brunel,D.;Micropor.Mesopor. Mater.,1999, 27, 329. [Google Scholar] [Crossref]

25. ShanthanRao,P.;Venkataratnam,R. V.;TetrahedronLett.,1991,32, 5821. [Google Scholar] [Crossref]

26. Lehnert,W.;Tetrahedron,1974,30, 301. [Google Scholar] [Crossref]

27. SaeedAbaee, M.; Mojtahedi, M.M.; Zahedi, M.M.; Khanalizadeh, G.;ARKIVOC,2006,XV,48. [Google Scholar] [Crossref]

28. a) Jones, G.; Org. Reac., 1967, 15, 204. b) Wang, Y.; Shang, Z.; Wu, T.; Fan, J.;Ohsaka, T.; J. Mol.Catal. A: Chem., 2006, 253, 212. c) Morrison, D. W.; Forbes,D.C.; Davis,J. H.;Tetrahedron Lett.,2001, 42, 6053. [Google Scholar] [Crossref]

29. Prajapati,P.;Sindhu,J.S.; J.Chem. Soc.,Perkin Trans-I,1993, 739. [Google Scholar] [Crossref]

30. Yamashita,K.;Tanaka,T.;Hayashi,M.;Tetrahedron,2005,61, 7981. [Google Scholar] [Crossref]

31. Leelavathi,P.; Kumar,S. R.; J. Mol.Catal.A:Chem., 2005,240, 99. [Google Scholar] [Crossref]

32. Reddy, T.I.;Varma, R.S.; TetrahedronLett.,1997,38, 1721. [Google Scholar] [Crossref]

33. Sameer.A;, MutaharAIAns;, SangitaSM;,Asian Journal of green Chemistry,9(6),2025,818-832. [Google Scholar] [Crossref]

34. Rong,L.;Li,X.;Wang,H.;Shi,D.;Tu,S.;Zhuang,Q.;Syn.Comm.,2006,36, 2407. [Google Scholar] [Crossref]

35. Ren,Y.; Cai,C.; Syn. Comm., 2009, 39,2001. [Google Scholar] [Crossref]

36. Wang,W.J.;Cheng,W.P.;Shao,L.L.;Liu,C.H.;Yang,J.G.;Kinetics& Catalysis, 2009, 50,186. [Google Scholar] [Crossref]

37. Chang,Z.;Zhu, H.;Wu, C.;Xing, J.; Dou, X.; Org.Biomol. Chem.;2021, 19, 785. [Google Scholar] [Crossref]

38. Periklis X. Kolagkis.; Stamatis K. Serviou.; Naya A. Stini, Vera P. Demertzidou.; Efthymios T. Poursaitidis.; Eirini M. Galathri,; Olga G. Mountanea.; Elpida Skolia and Christoforos G. Kokotos.; Org.Biomol.Chem, 2024, 22(41): 8293-8299 [Google Scholar] [Crossref]

39. Smal,M.;Chenug,H.T.A.;Davis,P.E.;J.Chem.Soc.,PerkinTrans-I,1986, 747. [Google Scholar] [Crossref]

40. Roth,B.;Falco,E.A.;Hitchings,G.H.;Bushby,S.R.M.;J.Med.Pharm.Chem.,1962, 5, 1103. [Google Scholar] [Crossref]

41. Ashok,S.P.;Aravind,S.B.; Devkate,S. S.;Asian.J.Chem.,2020,32(3), 575. [Google Scholar] [Crossref]

42. Youseff,A.M.;Mohamed,H.M.;Czezowski,C.;Ata,A.;Abd-El-Aziz,A.S.; [Google Scholar] [Crossref]

43. Heterocycles,2006,68(2),347. [Google Scholar] [Crossref]

44. Guchhait, S. K.; Sisodiya, S. K.; Saini, M.; Shah, Y. V.; Kumar, G.; Daniel, D. P.; Hura, N.; Chaudhary, V.; J. Org. Chem., 2018, 83(10), 5807. [Google Scholar] [Crossref]

45. Naveen,S.;Lakshmi,S.;Dinesh,M.;Alpesh,P.;Anamik,S.;Sridhar,M.A.; Prasad, J. S.; J. Chem. Crystallogr. 2007, 37, 733. [Google Scholar] [Crossref]

46. Ashok, S. P.; Aravind, S. B.; Devkate, S. S.; Asian. J. Chem., 2020, 32(3), 575. [Google Scholar] [Crossref]

47. Ruger, N.; Fassauer, G. M.; Bock, C.; Emmrich, T.; Bodtke, A.; Link, A.; Mol. Divers, 2017, 21(1), 9. [Google Scholar] [Crossref]

48. Naveen, S.; Lakshmi, S.; Dinesh, M.; Alpesh, P.; Anamik, S.; Sridhar, M. A.; Prasad, J. S.; J. Chem. Crystallogr., 2007, 37, 733. [Google Scholar] [Crossref]

49. Guchhait, S. K.; Sisodiya, S.; Saini, M.; Shah, Y. V.; Kumar, G.; Daniel, D. P.; Hura, N.; Chaudhary, V.; J. Org. Chem., 2018, 83(10), 5807. [Google Scholar] [Crossref]

50. Porter, D. W.; Bardley, M.; Brown, Z.; Charlton, S. J.; Cox, B.; Hunt, P.; Janus, D.; Lewis, S.; Oakey, P.; Connor, D. O.; Reilly, J.; Smith, N.; Press, N. J.; Bioorg. Med. Chem. Lett., 2014, 24, 3285. [Google Scholar] [Crossref]

51. Youseff, A. M.; Mohamed, H. M.; Czezowski, C.; Ata, A.; Abd-El-Aziz, A. S.; Heterocycles, 2006, 68(2), 347. [Google Scholar] [Crossref]

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