Home Articles List Article Information
Iranian Chemical Communication
Journal Archive
Volume Volume 7 (2019)
Volume Volume 6 (2018)
Volume Volume 5 (2017)
Volume Volume 4 (2016)
Volume Volume 3 (2015)
Volume Volume 2 (2014)
Volume Volume 1 (2013)
Hoseini Rad, M., Ghasemzadeh, M., Sharif, M. (2019). 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. Iranian Chemical Communication, 7(Issue 4. pp. 352-471), 390-397. doi: 10.30473/icc.2019.42092.1471
Masomeh Hoseini Rad; Mohammad Ali Ghasemzadeh; Mahboubeh Sadat Sharif. "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". Iranian Chemical Communication, 7, Issue 4. pp. 352-471, 2019, 390-397. doi: 10.30473/icc.2019.42092.1471
Hoseini Rad, M., Ghasemzadeh, M., Sharif, M. (2019). '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', Iranian Chemical Communication, 7(Issue 4. pp. 352-471), pp. 390-397. doi: 10.30473/icc.2019.42092.1471
Hoseini Rad, M., Ghasemzadeh, M., Sharif, M. 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. Iranian Chemical Communication, 2019; 7(Issue 4. pp. 352-471): 390-397. doi: 10.30473/icc.2019.42092.1471

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

Article 4, Volume 7, Issue 4. pp. 352-471, July and August 2019, Page 390-397  XML PDF (834 K)
Document Type: Original Research Article
DOI: 10.30473/icc.2019.42092.1471
Authors
Masomeh Hoseini Rad1; Mohammad Ali Ghasemzadeh 2; Mahboubeh Sadat Sharif3
1Department of Chemistry, Qom Branch, Islamic Azad University, Qom, I. R. Iran
2Department of Chemistry, Qom Branch, Islamic Azad University, Qom, P.O. Box 37491-13191. R. Iran
3Department of Chemistry, Faculty of Science, Qom Branch, Islamic Azad University, Qom, Iran
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

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
Keywords
multi-component reaction; metal–organic framework; pyrrole; Zn (BDC); catalyst
Main Subjects
Organic chemistry
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.

Statistics
Article View: 81
PDF Download: 89