Abstract
A specific efficient method of synthesis of biologically active analogues of the title compound from acetylene dicarboxylate, aniline and various aromatic aldehydes catalyzed by citric acid by one-pot mortar-pestle grinding is described. The short time synthesis is characterized by high yields and comparable with the similar mechano-chemical process of planetary ball-milling. Easy isolation of the products without involving separation methods makes this green synthesis to be cost-efficient.
Similar content being viewed by others
REFERENCES
Hamzah, A.S., Shaameri, Z., and Goksu, S., J. Chem., 2013, p. 2. https://doi.org/10.1155/2013/250381
Fukuda, T., Sudoh, Y., Tsuchiya, Y., Okuda, T., and Igarashi, Y., J. Nat. Prod., 2014, vol. 77, p. 813. https://doi.org/10.1021/np400910r
Yu, C.Y. and Huang, M.H., Org. Lett., 2006, vol. 8, p. 3021. https://doi.org/10.1021/ol0609210
Zheng, X., Cheng, Q., Yao, F., Wang, X., Kong, L., Cao, B., Xu, M., Lin, S., Deng, Z., Chooi, Y.H., and You, D., Proc. Nati. Acad. Sci. USA., 2017, vol. 114(16), p. 4135. https://doi.org/10.1073/pnas.1701361114
Shorvon, S., The Lancet, 2001, vol. 358, p. 1885. https://doi.org/10.1016/S0140-6736(01)06890-8
Löscher, W. and Richter, A., Eur. J. Pharmacol., 2000, vol. 391, p. 251. https://doi.org/10.1016/S0014-2999(00)00105-9
Malykh, A.G. and Sadaie, M.R., Drugs, 2010, vol. 70, p. 287. https://doi.org/10.2165/11319230-000000000-00000
Gouliaev, A.H. and Senning, A., Brain Res. Rev., 1994, vol. 19, p. 180. https://doi.org/10.1016/0165-0173(94)90011-6
Johari, S.A., Mohtar, M., Mohamad, S.A.S., Mohammat, M.F., Sahdan, R., Mohamed, A., and Ridhwan, M.J.M., Biomed. Res. Int., 2017. https://doi.org/10.1155/2017/8032865
Johari, S.A., Mohtar, M., Mohamad, S.A.S., Sahdan, R., Shaameri, Z., Hamzah, A.S. and Mohammat, M.F., Biomed. Res. Int., 2015, https://doi.org/10.1155/2015/823829
Abdul Rashid, F.N.A., Mohammat, M.F., Shaameri, Z., and Hamzah, A.S., Org. Commun., 2019, vol. 12, p. 121. https://doi.org/10.25135/acg.oc.62.19.07.1323
Mohammat, M.F., Shaameri, Z., and Hamzah, A.S., Molecules, 2019, vol. 14, p. 250. https://doi.org/10.3390/molecules14010250
Mohammat, M.F., Najim, N., Mansor, N.S., Sarman, S., Shaameri, Z., Zain, M.M., and Hamzah, A.S., Arkivoc, 2011, p. 429. https://doi.org/10.3998/ark.5550190.0012.932
Khaligh, N.G., Mihankhah, T., and Johan, M.R., Synth. Commun., 2019, vol. 49, p. 1334. https://doi.org/10.1080/00397911.2019.1601225
Khaligh, N.G., Mihankhah, T., Johan, M.R., and Titinchi, S.J.J., Green Process Synth., 2019, vol. 8, p. 373. https://doi.org/10.1515/gps-2019-0004
Will, H., Scholz, P., and Ondruschka, B., Chemie Ingenieur Technik, 2002, vol. 74, p. 1057. https://doi.org/10.1002/1522-2640(20020815)
Lew, A., Krutzik, P.O., Hart, M.E., and Chamberlin, A.R., J. Comb. Chem., 2002, vol. 4, p. 95. https://doi.org/10.1021/cc010048o
Larhed, M., Moberg, C., and Hallberg, A., Acc. Chem. Res., 2002, vol. 35, p. 717. https://doi.org/10.1021/ar010074v
Varma, R.S., Advances In Green Chemistry: Chemical Syntheses Using Microwave Irradiation, Bangalore: Astrazeneca Research Foundation India, 2002, p. 46.
Funding
The authors thanks Ministry of Higher Education for the financial support (600-IRMI/FRGS 5/3 (398/2019).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
No conflict of interest was declared by the authors.
Rights and permissions
About this article
Cite this article
Mohammat, M.F., Safyudin, U., Rashid, F.N.A.A. et al. Synthesis of Ethyl 3-Methyl-4,5-dioxo-1,2-diphenylpyrrolidine-3-carboxylate Analogues Using Green and Expeditious Grinding Method. Russ J Gen Chem 91, 2272–2279 (2021). https://doi.org/10.1134/S1070363221110141
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363221110141