Multi-component synthesis of spiro[indoline-3,4'-pyrrolo[3,4-c]pyrazoles] using Zn(BDC) metal-organic frameworks as a green and efficient catalyst

Hoseini Rad, Masomeh; Ghasemzadeh, Mohammad Ali; Sharif, Mahboubeh Sadat

doi:10.33945/SAMI/ECC.2019.4.3

Document Type : Original Research Article

Authors

¹ Department of Chemistry, Qom Branch, Islamic Azad University, Qom, I. R. Iran

² Department of Chemistry, Qom Branch, Islamic Azad University, Qom, P.O. Box 37491-13191. R. Iran

³ Department of Chemistry, Faculty of Science, Qom Branch, Islamic Azad University, Qom, Iran

10.33945/SAMI/ECC.2019.4.3

Abstract

In this research, a series of spiro compounds was efficiently synthesized via one-pot multi component reactions of isatins, aryl amines, dimethyl acetylenedicarboxylate and hydrazine in the presence of Zn(BDC) MOF as catalyst. The key superiority of this process is high yields, easy work-up, short reaction times, and purification of the products by the non-chromatographic system. The study of the reusability of the catalyst showed that the Zn(BDC) can be readily recovered and reused six times with a slight decrease in its activity. Furthermore, the catalyst was characterized by SEM, EDX, FT-IR and XRD analysis.

Graphical Abstract

Keywords

References

[1] B. Jiang, T. Rajale, W. Wever, S. Tu, G. Li, Chem. Asian J., 2010, 5, 2318-2335.

[2] V.N. Este ´vez, M. Villacampa , J.C. Menendez, Chem. Soc. Rev., 2014, 43, 4633-4657.

[3] E. Baltazzi, L.I. Krimen, Chem. Rev., 1963, 63, 511-556.

[4] C. Galliford, K.A. Scheidt, J. Org. Chem., 2007, 72, 1811-1813.

[5] a) M. Keshavarz, Iran. Chem. Commun., 2018, 6, 134-142; b) H.A. Oskooie, M.M. Heravi, N. Karimi, H. Hamidi, Synth.Commun., 2011, 41, 3344-3350.

[6] N. Azizi, A. Khajeh-Amiri, H. Ghafuri, M. Bolourtchian, M. R. Saidi, Synlett, 2009, 2245-2248,

[7] T. Maehara, R. Kanno, S. Yokoshima, T. Fukuyama, Org. Lett., 2012, 14, 1946-1948.

[8] L. Eberlin, B. Carboni, A. Whiting, J. Org. Chem., 2015, 80, 6574-6583.

[9] S.R.K. Minkler, N.A. Isley, D.J. Lippincott, N. Krause, B.H. Lipshutz, Org. Lett., 2014, 16, 724-726.

[10] Y. Lu, M. Tonigold, B. Bredenkotter, D. Volkmer, J. Hitzbleck G. Langstein, Z. Anorg. Allg. Chem., 2008, 634, 2411-2417.

[11] L. Mar, M. Iglesias, N. Snejko, E. Guti¦rrez-Puebla, M. ÝngelesMonge, Chem. Eur. J., 2016, 22, 6654-6665.

[12] a) R. Zou, A. Abdel-Fattah, H. Xu, Y. Zhao, D.D. Hickmott, Cryst. Eng. Comm., 2010, 12, 1337-1353; b) Z. Arzehgar, S. Sajjadifar, M.H. Fekri, Chem. Method., 2019, 3, 251-260; c) Z. Arzehgar, S. Sajjadifar, H. Arandiyan, Asian J. Green Chem., 2019, 3. 43-52.

[13] S.R. Batten, S.M. Neville, D.R. Turner, Coordination Polymers, Design, Analysis and Application, RSC publishing, 1st Edition, Cambridge, pp., 471, 2009.

[14] J.L.C. Rowsell, O.M. Yaghi, Micropor. Mesopor. Mater., 2004, 73, 3-14.

[15] K.M. Thomas, Dalton Trans., 2009, 11, 1487-1505.

[16] R.J. Kuppler, D.J. Timmons, Q-R. Fang, J-R. Li, T.A. Makal, M.D. Young, D. Yuan, D. Zhao, W. Zhuang, H-C. Zhou, Coord. Chem. Rev., 2009, 253, 3042-3066.

[17] D.K. Kumar, D.A. Jose, P. Dastidar A. Das, Chem. Mater., 2004, 16, 2332-2335.

[18] M. A. Ghasemzadeh, M. H. Abdollahi-Basir,B. Mirhosseini-Eshkevari, Green. Chem. Lett. Rev., 2018, 11, 47-53.

[19] M.A. Ghasemzadeh, B. Mirhosseini-Eshkevari, M.H. Abdollahi-Basr, Comb. Chem. High Throughput Screen, 2016, 19, 592-601.

[20] M.A. Ghasemzadeh, M.H. Abdollahi-Basir, M. Babaei, Green. Chem. Lett. Rev., 2015, 8, 40-49.

[21] B. Mirhosseini-Eshkevari, M.A. Ghasemzadeh, J. Safaei-Ghomi, Res. Chem. Intermed, 2015, 41, 703-708.

[22] M.A. Ghasemzadeh, M.H. Abdollahi-Basir, B. Mirhosseini-Eshkevari, Green. Chem. Lett. Rev., 2018, 11, 47-53.

[23] O. Solomon, W.R.S. Umar, H.S. Wara, A.S. Yakubu, M.M. Azubuike, M.A. Mary, H. Louis, Prog. Chem. Biochem. Res., 2018, 1, 29-39.

[24] A.U. Itodo, O.M. Itodo, E. Iornumbe, M.O. Fayomi, Prog. Chem. Biochem. Res., 2018, 1, 50-59.

[25] K.Kh. Alisher, T.S. Khamza, Y.Sh. Ikbol, Prog. Chem. Biochem. Res., 2019, 2, 1-5.

Eurasian Chemical Communications

Multi-component synthesis of spiro[indoline-3,4'-pyrrolo[3,4-c]pyrazoles] using Zn(BDC) metal-organic frameworks as a green and efficient catalyst

References

References

Volume 1, Issue 4
July and August 2019
Pages 344-351

Multi-component synthesis of spiro[indoline-3,4'-pyrrolo[3,4-c]pyrazoles] using Zn(BDC) metal-organic frameworks as a green and efficient catalyst

References

References

Volume 1, Issue 4July and August 2019Pages 344-351

Volume 1, Issue 4
July and August 2019
Pages 344-351