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A continuous-flow procedure for the synthesis of 4-Benzylidene-pyrazol-5-one derivatives

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Abstract

A two-step flow reactor has been set up for an expeditious synthesis of 4-benzylidene-pyrazol-5-one derivatives. This procedure involved cyclization of aromatic hydrazine/β-keto ester and subsequent Knoevenagel condensation reaction with aromatic aldehydes in tandem without isolation of intermediates. Residence time was reduced to less than 2 min in total through conducting this reaction at a relatively high temperature. Accordingly, 15 samples were achieved and isolated in moderate to excellent yields.

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References

  1. A. Weissberger. In: Wiley, R. H., Wiley, P. (eds.) The Chemistry of Heterocyclic Compounds: Pyrazolinones, Pyrazolidones and Derivatives. Wiley, New York; 1964

  2. S. Scheibye, A. A. El-Barbary, S. O. Lawesson, H. Fritz, G. Rihs. Tetrahedron 1982; 38, 3753

  3. Y. Kakiuchi, N. Sasaki, M. Satoh-Masuoka, H. Murofushi, Murakami-Murofushi, K. Biochem. Biophys. Res. Commun. 2004; 320, 1351

  4. S. P. Hiremath, K. Rudresh, A. R. Saundane. Indian J. Chem. 2002; 41B, 394

  5. In: H. A. Lubs (ed.) The Chemistry of Synthetic Dyes and Pigments. American Chemical Society, Washington, DC; 1970

  6. Joerg S, Reinhold G, Joachim OS, Robert S, Klaus L, Offen G (1988) Chem Abstr 108:167465 DE3, 625

  7. A. B. Uzoukwu. Polyhedron 1993; 12, 2719

  8. G. Desimoni, L. Astolfi, M. Cambieri, A. Gamber, G. Tacconi. Tetrahedron 1973; 29, 2627

  9. W. S. Hamama. Synth. Commun. 2001; 31, 1335

  10. M. M. Mojtahedi, M. R. Jalali, M. S. Abaee, M. Bolourtchian. Heterocycl. Commun. 2006; 12, 225

  11. B. R. Vaddula, R. S. Varma, J. Leazer. Tetrhedron Lett. 2013; 54, 1538

  12. M. M. Mojtahedi, M. Javadpour, M. S. Abaee. Ultrason. Sonochem. 2008; 15, 828

  13. M. X. Guo, J. X. Guo, D. Z. Jia, H. Liu, L. Liu, A. J. Liu, F. Li. J. Mol. Struct. 2013; 1035, 271

  14. Ahmad N (2011) Acta Ciencia Indica. Chemistry 37:5

    CAS  Google Scholar 

  15. E. Garcia-Egido, S. Y. Wong, B. H. Warrington. Lab Chip 2002; 2, 31

  16. M. Fernandez-Suarez, S. Y. Wong, B. H. Warrington. Lab Chip 2002; 2, 170

  17. E. Garcia-Egido, V. Spikmans, S. Y. Wong, B. H. Warrington. Lab Chip 2003; 3, 73

  18. D. Obermayer, T. N. Glasnov, C. O. Kappe. J. Org. Chem. 2011; 76, 6657

  19. J. Pelleter, F. Renaud. Org. Process. Res. Dev. 2009; 13, 698

  20. M. S. K. Youssef, S. A. M. Metwally, M. A. El-Mahraby, M. I. Younes. J. Heterocyclic Chem. 1984; 21, 1747

  21. P. Sun, D. Yang, W. Wei, X. Sun, W. Zhang, H. Zhang, Y. Wang, H. Wang. Tetrahedron 2017; 73, 2022

  22. V. Hessel (2009). Chem. Eng. Technol. 32, 1655

  23. B. Wahab, G. Ellames, S. Passey, P. Watts (2010). Tetrahedron 66, 3861

  24. E. Riva, S. Gagliardi, C. Mazzoni, D. Passarella, A. Rencurosi, D. Vigo, A. Rencurosi (2010). Tetrahedron 66, 3242

  25. Z. Q. Yu, Y. W. Lv, C. M. Yu (2012). Org. Process. Res. Dev. 16, 1669

  26. J. Wegner, S. Ceylan, A. Kirschning. Adv. Synth. Catal. 2012; 354, 17

  27. C. Wiles, P. Watts. Green Chem. 2012; 14, 38

  28. Z. Q. Yu, Y. W. Lv, C. M. Yu, W. K. Su. Tendrahedron Lett. 2013; 54, 1261

  29. Z. Q. Yu, Y. W. Lv, C. M. Yu, W. K. Su. Org. Process Res. Dev. 2013; 17, 438

  30. C. Wiles, P. Watts. Green Chem. 2014; 16, 55

  31. D. Cambié, C. Bottecchia, N. J. W. Straathof, V. Hessel and T. Noël. Chem. Rev. 2016; 116, 10276

  32. B. Gutmann, D. Cantillo and C. O. Kappe. Angew. Chem. Int. Ed. 2015; 54, 6688–6728

  33. J. Britton. J. Flow Chem. 2016; 6, 123

  34. S. Chada, D. Mandala and P. Watts. J. Flow Chem. 2017; 7, 37

  35. Y. W. Lv, Z. Q. Yu, W. K. Su. Org. Process. Res. Dev. 2011; 15, 471

  36. J. Yu, J. Xu, Z. Yu, Y. Jin, J. Li, Y. Lv. J. Flow Chem. 2017; 7, 33

  37. J. Xu, J. Yu, Y. Jin, J. Li, Z. Yu, Y. Lv. Chem. Eng. Process 2017; 121, 144

  38. W. P. Bula, W. Verboom, D. N. Reinhoudt, H. J. G. E. Gardeniers. Lab Chip 2007; 7, 1717

  39. E. G. Moschetta, S. Negretti, K. M. Chepiga, N. A. Brunelli, Y. Labreche, Y. Feng, F. Rezaei, R. P. Lively, W. J. Koros, H. M. L. Davies, C. W. Jones. Angew. Chem. Int. Ed. 2015; 54, 6470

  40. M. Lopez-Pastor, A. Dominguez-Vidal, M. J. Ayora-Canada, T. Laurell, M. Valcarcel, B. Lendl. Lab Chip 2007; 7, 126

  41. H. Seyler, S. Haid, T.-H. Kwon, D. J. Jones, P. Baeuerle, A. B. Holmes, W. W. H. Wong. Aust. J. Chem. 2013; 66, 151

  42. V. Pandarus, G. Gingras, F. Beland, R. Ciriminna, M. Pagliaro. Catal. Sci. Technol. 2011; 1, 1600

  43. M. Tarleton, A. McCluskey. Tetrahedron Lett. 2011; 52, 1583

  44. N. Nikbin, P. Watts. Org. Process. Res. Dev. 2004; 8, 942

  45. R. Munirathinam, J. Huskens, W. Verboom. Adv. Synth. Catal. 2015; 357, 1093

  46. K. Suzdalev, M. Babakova. Russ. J. Org. Chem. 2005; 41, 233

  47. Z. Han, X. Liang, Y. Wang, J. Qing, L. Cao, L. Shang, Z. Yin. Eur. J. Med. Chem. 2016; 116, 147

  48. R. Ramajayam, K.-P. Tan, H.-G. Liu, P.-H. Liang, Bioorg. Med. Chem. 2010; 18, 7849

  49. M. Parveen, S. Azaz, A. M. Malla, F. Ahmad, M. Ahmad, M. Gupta. RSC Adv. 2016; 6, 148

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Acknowledgments

Financial support from the National Science Foundation of China (21476128) is gratefully acknowledged.

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Authors and Affiliations

  1. College of Chemical and Material Engineering, Quzhou University, Quzhou, 324000, People’s Republic of China

    Jiangang Yu, Jianguo Xu, Jie Li, Yi Jin, Wanghui Xu & Yanwen Lv

  2. Key Laboratory of Pharmaceutical Engineering of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, 310014, People’s Republic of China

    Zhiqun Yu

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  1. Jiangang Yu
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  2. Jianguo Xu
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  3. Jie Li
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  4. Yi Jin
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  5. Wanghui Xu
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  6. Zhiqun Yu
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  7. Yanwen Lv
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Correspondence to Yanwen Lv.

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Yu, J., Xu, J., Li, J. et al. A continuous-flow procedure for the synthesis of 4-Benzylidene-pyrazol-5-one derivatives. J Flow Chem 8, 29–34 (2018). https://doi.org/10.1007/s41981-018-0003-8

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  • DOI: https://doi.org/10.1007/s41981-018-0003-8

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