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Survey reactivity of 2-aminopyridine and Meldrum’s acid in the presence of aryl glyoxals or aryl aldehydes; ethyl 2-(3-aryl imidazo[1,2-a]pyridin-2-yl)acetates versus ethyl 3-aryl-3-(pyridin-2-ylamino)propanoates

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Abstract

The aim of present investigation is survey reactivity of 2-aminopyridine and Meldrum’s acid in the presence of aryl glyoxals or aryl aldehydes. The ethyl 2-(3-aryl imidazo[1,2-a]pyridin-2-yl)acetates were successfully synthesized by reaction of 2-aminopyridine, Meldrum’s acid, and aryl glyoxals, while the ethyl 3-aryl-3-(pyridin-2-ylamino)propanoates were synthesized in the presence of aryl aldehydes. The reactions are performed in ethanol, catalyzed by acetic acid at reflux and microwave conditions.

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References

  1. S. Park, H. Kim, J.Y. Son, K. Um, S. Lee, Y. Baek, P.H. Lee, J. Org. Chem. 82, 10209 (2017)

    Article  CAS  Google Scholar 

  2. Z.T. Bhutia, P.C. Panjikar, S. Iyer, A. Chatterjee, M. Banerjee, ACS Omega 5, 13333 (2020)

    Article  CAS  Google Scholar 

  3. S.K. Samanta, M.K. Bera, Org. Biomol. Chem. 17, 6441 (2019)

    Article  Google Scholar 

  4. Y. Katsura, S. Nishino, Y. Inoue, M. Tomoi, H. Takasugi, Chem. Pharm. Bull. 40, 371 (1992)

    Article  CAS  Google Scholar 

  5. Y. Rival, G. Grassy, G. Michel, Chem. Pharm. Bull. 40, 1170 (1992)

    Article  CAS  Google Scholar 

  6. V.R. Mallemula, N.N. Sanghai, V. Himabindu, A.K. Chakravarthy, Res. Chem. Intermed. 41, 2125 (2015)

    Article  CAS  Google Scholar 

  7. Y. Chen, S. Wang, L. Zhao, C. Rong, T. Liu, H. Sun, G. Zhong, Synthesis 50, 3169 (2018)

    Article  CAS  Google Scholar 

  8. S. Ponnala, S.T.V.S.K. Kumar, B.A. Bhat, D.P. Sahu, Synth. Commun. 35, 901 (2005)

    Article  CAS  Google Scholar 

  9. O.P.S. Patel, K.N. Nitesh, J.L. Lesetja, C.D. Bhaskar, K. Anil, Adv. Synth. Catal. 362, 4226 (2020)

    Article  CAS  Google Scholar 

  10. T. Mase, H. Arima, K. Tomioka, T. Yamada, K. Murase, J. Med. Chem. 29, 386 (1986)

    Article  CAS  Google Scholar 

  11. L. Albrecht, A. Albrecht, L.K. Ransborg, K.A. Jørgensen, Chem. Sci. 2, 1273 (2011)

    Article  CAS  Google Scholar 

  12. J.A. Vega, J.J. Vaquero, J.A. Builla, J. Ezquerra, C. Hamdouchi, Tetrahedron 55, 2317 (1999)

    Article  CAS  Google Scholar 

  13. V.A. Peshkov, A.A. Peshkov, O.P. Pereshivko, K. Van Hecke, L.L. Zamigaylo, E.V.V. Eycken, N.Y. Gorobets, ACS. Comb. Sci. 16, 535 (2014)

    Article  CAS  Google Scholar 

  14. B. Dubinsky, D.A. Shriver, P.J. Sanfilippo, J.B. Press, A.J. Tobia, M.E. Rosenthale, Drug. dev. Res. 2, 277 (1990)

    Article  Google Scholar 

  15. A.K. Bagdi, S. Santra, K. Monir, A. Hajra, Chem. Commun. 51, 1555 (2015)

    Article  CAS  Google Scholar 

  16. M.H. Fisher, A. Lusi, J. Med. Chem. 15, 982 (1972)

    Article  CAS  Google Scholar 

  17. H. Tomoda, T. Hirano, S. Saito, T. Mutai, K. Araki, Bull. Chem. Soc. JPN. 72, 1327 (1999)

    Article  CAS  Google Scholar 

  18. H.Y. Huang, R.S. Hou, H.M. Wang, L.C. Chen, J. Chin. Chem. Soc. 51, 1377 (2004)

    Article  CAS  Google Scholar 

  19. N. Etivand, J. Khalafy, A.P. Marjani, Res. Chem. Intermed. 45, 3379 (2019)

    Article  CAS  Google Scholar 

  20. M. Pordel, H. Chegini, S. Ramezani, M. Daee, J. Mol. Str. 11, 105 (2017)

    Article  Google Scholar 

  21. M. Tajbakhsh, M. Farhang, R. Hosseinzadeh, Y. Sarrafi, RSC. Adv. 4, 23116 (2014)

    Article  CAS  Google Scholar 

  22. H. Kim, M. Byeon, E. Jeong, Y. Baek, S.J. Jeong, K. Um, P.H. Lee, Adv. Syn. Catal. 361, 2094 (2019)

    Article  CAS  Google Scholar 

  23. U.B. Karale, S. Kalari, J. Shivakumar, V.B. Makane, D.A. Babar, R.P. Thakare, H.B. Rode, RSC. Adv. 6, 65095 (2016)

    Article  CAS  Google Scholar 

  24. B. Mu, J. Li, D. Zou, Y. Wu, J. Chang, Y. Wu, Org. Lett. 18, 5260 (2016)

    Article  CAS  Google Scholar 

  25. T. Borodina, I. Marchenko, D. Trushina, Y. Volkova, V. Shirinian, I. Zavarzin, T. Bukreeva, J. Pharm. Pharm. 70, 1164 (2018)

    Article  CAS  Google Scholar 

  26. Y. Wang, B. Zhang, Y. Zheng, Q. Ma, Q. Sui, X. Lei, Tetrahedron 75, 1064 (2019)

    Article  CAS  Google Scholar 

  27. R.K. Mondal, S. Dhibar, P. Mukherjee, A.P. Chattopadhyay, R. Saha, B. Dey, RSC. Adv. 6, 61966 (2016)

    Article  CAS  Google Scholar 

  28. S.R. Choudhury, J. Bhattacharyya, S. Das, B. Dey, S. Mukhopadhyay, L.P. Lu, M.L. Zhu, Acta. Cryst. E63, m1331 (2007)

    Google Scholar 

  29. S.R. Choudhury, B. Dey, S. Das, P. Gamez, A. Robertazzi, K.T. Chan, H.M. Lee, S. Mukhopadhyay, J. Phys. Chem. A. 113, 1623 (2009)

    Article  CAS  Google Scholar 

  30. A. Das, S.R. Choudhury, B. Dey, S.K. Yalamanchili, M. Helliwell, P. Gamez, S. Mukhopadhyay, C. Estarellas, A. Frontera, J. Phys. Chem. B. 114, 4998 (2010)

    Article  CAS  Google Scholar 

  31. V.M. Bangade, B.C. Reddy, P.B. Thakur, B.M. Babu, H.M. Meshram, Tetrahedron Lett. 54, 4767 (2013)

    Article  CAS  Google Scholar 

  32. H. Yan, Y. Wang, C. Pan, H. Zhang, S. Yang, X. Ren, G. Huang, Eur. J. Org. Chem. 13, 2754 (2014)

    Article  Google Scholar 

  33. H. Su, L. Wang, H. Rao, H. Xu, Org. Lett. 19, 2226 (2017)

    Article  CAS  Google Scholar 

  34. L. Veltri, P. Russo, T. Prestia, P. Vitale, R. Romeo, B. Gabriele, J. Catal. 386, 53 (2020)

    Article  CAS  Google Scholar 

  35. Q. Huang, H. Dong, B. Li, W. Hu, Y. Wang, Tetrahedron 76, 130998 (2020)

    Article  CAS  Google Scholar 

  36. P. Ghosh, S. Samanta, S. Ghosh, S. Jana, A. Hajra, Tetrahedron Lett. 61, 152581 (2020)

  37. S. Bhunia, P. Ghosh, S.R. Patra, Adv. Synth. Catal. 362, 3664 (2020)

    Article  CAS  Google Scholar 

  38. E.P.A. Talbot, M. Richardson, J.M. McKenna, F.D. Toste, Adv. Synth. Catal. 356, 687 (2014)

    Article  CAS  Google Scholar 

  39. F. Mert-Balci, J. Conrad, U. Beifuss, Arch. Org. Chem, iii, 243 (2012)

  40. H. Mehrabi, F. Alizadeh-Bami, A. Meydani, S. Besharat, ARKIVOC 8, 86 (2021)

    Article  Google Scholar 

  41. H. Mehrabi, M. Hajipour, F. Rezazadeh-Jabalbarezi, F. Alizadeh-Bami, J. Heterocycl. Chem. 57, 3361 (2020)

    CAS  Google Scholar 

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Acknowledgements

We are thankful to the Office of Graduate Studies of Vali-e-Asr University of Rafsanjan for partial support of this work.

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Correspondence to Hossein Mehrabi.

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Asadi, S., Zebarjad, M., Masoudi, H. et al. Survey reactivity of 2-aminopyridine and Meldrum’s acid in the presence of aryl glyoxals or aryl aldehydes; ethyl 2-(3-aryl imidazo[1,2-a]pyridin-2-yl)acetates versus ethyl 3-aryl-3-(pyridin-2-ylamino)propanoates. Res Chem Intermed 48, 251–265 (2022). https://doi.org/10.1007/s11164-021-04554-z

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