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Vol. 34 No. 6 (2022): Vol 34 Issue 6

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An Ecofriendly and Efficient Approach through Sodium Oxalate Catalyst for the Synthesis of Azomethines and α-Aminonitriles Ligands Employing Aqueous Medium

https://doi.org/10.14233/ajchem.2022.23715
Bikramjit Singh
Department of Chemistry, Guru Nanak College, Budhlada-151502, India
Jatinder Singh Aulakh
Department of Chemistry, Punjabi University, Patiala-147002, India
Baldev Singh
Department of Chemistry, Punjabi University, Patiala-147002, India

Corresponding Author(s) : Jatinder Singh Aulakh

chemiaulakh@gmail.com

Asian Journal of Chemistry, Vol. 34 No. 6 (2022): Vol 34 Issue 6

Abstract

An ecofriendly, efficient, inorganic salt catalyzed facile method has been developed for the synthesis of potential ligands azomethines and α-aminonitriles employing aqueous medium. This procedure involves the use of Zn(CN)2 an inexpensive, less toxic as compared to KCN, ecofriendly and readily available effective cyanide source. Cyanated products specially have been isolated in high yield on usual work-up procedure. In methanol and DMF solvents, all of the produced compounds were evaluated for in vitro antibacterial activity against certain bacterial and fungal strains. Among the compounds tested, b and g had the most promising antibacterial action against Bacillus subtilis. Furthermore, compounds a and c were discovered to be the most effective antifungal agents against Candida albicans.

Keywords

Hydrocyanation Azomethines Eco-friendly Schiff base
Singh, B., Singh Aulakh, J., & Singh, B. (2022). An Ecofriendly and Efficient Approach through Sodium Oxalate Catalyst for the Synthesis of Azomethines and α-Aminonitriles Ligands Employing Aqueous Medium. Asian Journal of Chemistry, 34(6), 1549–1554. https://doi.org/10.14233/ajchem.2022.23715
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References
  1. W. Qin, S. Long, M. Panunzio and S. Biondi, Molecules, 18, 12264 (2013); https://doi.org/10.3390/molecules181012264
  2. N. Kuyucak and A. Akcil, Miner. Eng., 50-51, 13 (2013); https://doi.org/10.1016/j.mineng.2013.05.027
  3. L.G. Buttke, J.R. Schueller, C.S. Pearson and K.D. Beyer, J. Phys. Chem. A, 120, 6424 (2016); https://doi.org/10.1021/acs.jpca.6b05208
  4. S. Nakamura, N. Sato, M. Sugimoto and T. Toru, Tetrahedron Asymm., 15, 1513 (2004); https://doi.org/10.1016/j.tetasy.2004.03.040
  5. S.P. Pathare and K.G. Akamanchi, Tetrahedron Lett., 53, 871 (2012); https://doi.org/10.1016/j.tetlet.2011.12.027
  6. D. Chaturvedi, A.K. Chaturvedi, N. Mishra and V. Mishra, Tetrahedron Lett., 53, 5398 (2012); https://doi.org/10.1016/j.tetlet.2012.07.117
  7. J. Jarusiewicz, Y. Choe, K.S. Yoo, C.P. Park and K.W. Jung, J. Org. Chem., 74, 2873 (2009); https://doi.org/10.1021/jo900163w
  8. Z. Li, Y. Ma, J. Xu, J. Shi and H. Cai, Tetrahedron Lett., 51, 3922 (2010); https://doi.org/10.1016/j.tetlet.2010.05.088
  9. X. Hu Ma, Y.; Li, Z., J. Organomet. Chem., 705, 70 (2012); https://doi.org/10.1016/j.jorganchem.2012.02.005
  10. F.C. Acosta, A.S. Exposito, P. de Armas and F.G. Tellado, Chem. Commun., 6839 (2009); https://doi.org/10.1039/B914151K
  11. S. Kobayashi and H. Ishitani, Chem. Rev., 99, 1069 (1999); https://doi.org/10.1021/cr980414z
  12. E.N. Jacobsen and P. Vachal, J. Am. Chem. Soc., 124, 10012 (2002); https://doi.org/10.1021/ja027246j
  13. B. Thirupathi, M.K. Patil and B.M. Reddy, Appl. Catal. A: Gen., 384, 147 (2010); https://doi.org/10.1016/j.apcata.2010.06.019
  14. B.T. Matsuo, P.H.R. Oliveira, J.T.M. Correia and M.W. Paixão, Org. Lett., 23, 6775 (2021); https://doi.org/10.1021/acs.orglett.1c02353
  15. Z. Li, Y. Du, H. Lu, A. Yang and J. Yang, Green Process. Synth., 8, 93 (2019); https://doi.org/10.1515/gps-2018-0017
  16. Y. Kamitori, M. Hojo, R. Masuda, T. Fujitani, S. Ohara and T. Yokoyama, J. Org. Chem., 53, 129 (1988); https://doi.org/10.1021/jo00236a026
  17. J.K. Ramussen and S.M. Heilmann, Org. Synth., 7, 521 (1990); http://www.orgsyn.org/Content/pdfs/procedures/CV7P0521.pdf
  18. R. Adams and I. Levine, J. Am. Chem. Soc., 45, 2373 (1923); https://pubs.acs.org/doi/pdfplus/10.1021/ja01663a020
  19. X. Wang, B. Zhi, J. Baum, Y. Chen, R. Crockett, L. Huang and S. Eisenberg, J. Org. Chem., 71, 4021 (2006); https://doi.org/10.1021/jo0602571
  20. M. Shevlin, Tetrahedron Lett., 51, 4833 (2010); https://doi.org/10.1016/j.tetlet.2010.07.045
  21. Z. Iqbal, A. Lyubimtsev and M. Hanak, Synlett, 15, 2287 (2008); https://doi.org/10.1055/s-2008-1078269
  22. M. Alterman, H.O. Anderson, N. Garej, G. Ahlsem, S. Lovgren, B. Classon, V.H. Danielson, I. Kvarnstnom, L. Vrang, T. Vnge, B. Samuelsson and A. Hallberg, J. Med. Chem., 42, 3835 (1999); https://doi.org/10.1021/jm9910371
  23. F. Jin and P.N. Confalone, Tetrahedron Lett., 41, 3271 (2000); https://doi.org/10.1016/S0040-4039(00)00384-1
  24. G.P. Ellis and T.M. Romney-Alxender, Chem. Rev., 87, 779 (1987); https://pubs.acs.org/doi/pdf/10.1021/cr00080a006
  25. X. Zhang, A. Xia, H. Chen and Y. Liu, Org. Lett., 19, 2118 (2017); https://doi.org/10.1021/acs.orglett.7b00732
  26. S. Shah and B. Singh, Tetrahedron Lett., 53, 151 (2012); https://doi.org/10.1016/j.tetlet.2011.10.154
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