Phthalimide-N-sulfonic acid and Isatin-N-sulfonic acid as highly efficient catalysts for the synthesis of bis-coumarins

Zare, Abdolkarim; Sanjideh, Jalal

doi:10.30473/icc.2018.4612

Document Type : Original Research Article

Authors

Abdolkarim Zare ¹
Jalal Sanjideh ²

¹ Department of Chemistry, Payame Noor University of Bushehr, Bushehr, Iran

² Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Iran

https://doi.org/10.30473/icc.2018.4612

Abstract

Two highly efficient protocols for the production of bis-coumarins under solvent-free conditions have been introduced. The reaction of 4-hydroxycoumarin (2 eq.) with arylaldehydes (1 eq.) using phthalimide-N-sulfonic acid (PhtSA) or isatin-N-sulfonic acid (IsSA), as solid-acid catalysts, afforded the mentioned compounds with good to excellent yields in short times.
Briefly, we have introduced two new SO3H-bearing solid-acid catalysts, entitled phthalimide-N-sulfonic acid and isatin-N-sulfonic acid, for the preparation of bis-coumarins. The advantages of the presented protocols include: high effectuality and generality of the catalysts, high to excellent yields, short reaction times, simple synthesis of the catalysts from available and inexpensive starting materials, easy work-up and purification of the products, relatively mild conditions, application of solvent-free technique, and good compliance with the green chemistry protocols.

Graphical Abstract

Keywords

Main Subjects

Organic chemistry

References

[1] M. Choudhary, N. Fatima, K.M. Khan, S. Jalil, S. Iqbal, Atta-ur-Rahman, Bioorg. Med. Chem.,2006, 14, 8066-8072.

[2] I. Kostova, G. Momekov, M. Zaharieva, M. Karaivanova, Eur. J. Med. Chem.,2005, 40, 542-551.

[3] K.M. Khan, S. Iqbal, M.A. Lodhi, G.M. Maharvi, Zia-Ullah, M.I. Choudhary, Atta-ur-Rahman, S. Perveen, Bioorg. Med. Chem.,2004, 12, 1963-1968.

[4] J.H. Lee, H.B. Bang, S.Y. Han, J.G. Jun, Tetrahedron Lett., 2007, 48, 2889-2892.

[5] H. Zhao, N. Neamati, H. Hong, H.A. Mazumder, S. Wang, S. Sunder, G.W.A. Milne, Y. Pommier, T.R. Burke, J. Med. Chem., 1997, 40, 242-249.

[6] C.-X. Su, J.-F. Mouscadet, C.-C. Chiang, H.-J. Tsai, L.-Y. Hsu, Chem. Pharm. Bull., 2006, 54, 682-686.

[7] I. Manolov, C. Maichle-Moessmer, I. Nicolova, N. Danchev, Arch. Pharm., 2006, 339, 319-326.

[8] N. Hamdi, M.C. Puerta, P. Valerga, Eur. J. Med. Chem.,2008, 43, 2541-2548.

[9] H. Ammar, S. Abid, S. Fery-Forgues, Dyes Pigm.,2008, 78, 1-7.

[10] A. Chandrasekhar, S. Padmanabhan, S. Seshadri, Dyes Pigm.,1986, 7, 13-21.

[11] B.D. Wagner, Molecules,2009, 14, 210-237.

[12] N. Iravani, M. Keshavarz, M. Mousavi, M. Baghernejad, Iran. J. Catal., 2015, 5, 65-71.

[13] K. Parvanak Boroujeni, P. Ghasemi, Z. Rafienia, Monatsh. Chem., 2014, 145, 1023-1026.

[14] R. Rezaei, M.R. Sheikhi, Res. Chem. Intermed., 2015, 41, 1283-1292.

[15] J. Albadi, A. Mansournezhad, S. Salehnasab, Res. Chem. Intermed., 2015, 41, 5713-5721.

[16] K. Tabatabeian, H. Heidari, A. Khorshidi, M. Mamaghani, N.O. Mahmoodi, J. Serb. Chem. Soc., 2012, 77, 407-413.

[17] A. Zhu, S. Bai, L. Li, M. Wang, J. Wang, Catal. Lett., 2015, 145, 1089-1093.

[18] E. Noroozizadeh, A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, R. Karamian, M. Asadbegy, S. Yari, S. H. Moazzami Farida, J. Iran. Chem. Soc., 2018, 15, 471-481.

[19] M. Zarei, M.A. Zolfigol, A.R. Moosavi-Zare, E. Noroozizadeh, J. Iran. Chem. Soc., 2017, 14, 2187-2198.

[20] S.S. Kauthale, S.U. Tekale, K.M. Jadhav, R.P. Pawar, Mol. Divers., 2016, 20, 763-770.

[21] A. Zare, H. Asvar, F. Zarei, M. Khalili, Z. Kordrostami, A.R. Moosavi-Zare, V. Khakyzadeh, J. Appl. Chem. Res.,2016, 10, 59-67.

[22] M. Maghsoudi, A. Zare, A.R. Moosavi-Zare, F. Raghbat, M.A. Zolfigol, J. Appl. Chem., 1396, 12, 197-208.

[23] Z. Tai, M.A. Isaacs, C.M.A. Parlett, A.F. Lee, K. Wilson, Catal. Commun., 2017, 92, 56-60.

[24] J. Dai, L. Zhu, D. Tang, X. Fu, J. Tang, X. Guo, C. Hu, Green Chem., 2017, 19, 1932-1939.

[25] M.A. Zolfigol, A. Khazaei, S. Alaie, S. Baghery, Can. J. Chem., 2017, 95, 560-570.

[26] A. Zare, M. Dashtizadeh, M. Merajoddin, Iran. Chem. Commun., 2015, 3, 208-217.

[27] M. Beyrati, A. Hasaninejad, Tetrahedron Lett., 2017, 58, 1947-1951.

[28] A. Zare, F. Monfared, Iran. Chem. Commun., 2014, 2, 1-13.

[29] F. Tamaddon, D. Azadi, J. Mol. Liq., 2018, 249, 789-794.

[30] A. Zare, Z. Nasouri, J. Mol. Liq., 2016, 216, 364-369.

[31] F. Shirini, M. Abedini, S. Zamani, H. Fallah Moafi, J. Nanostruct. Chem., 2015, 5, 123-130.

[32] M.A. Zolfigol, A.R. Moosavi-Zare, M. Zarei, C.R. Chim., 2014, 17, 1264-1267.

Iranian chemical communication

Phthalimide-N-sulfonic acid and Isatin-N-sulfonic acid as highly efficient catalysts for the synthesis of bis-coumarins

References

References

Volume 7, Issue 2, pp. 90-159, Serial No. 23
April 2019
Pages 139-145

Phthalimide-N-sulfonic acid and Isatin-N-sulfonic acid as highly efficient catalysts for the synthesis of bis-coumarins

References

References

Volume 7, Issue 2, pp. 90-159, Serial No. 23April 2019Pages 139-145

Volume 7, Issue 2, pp. 90-159, Serial No. 23
April 2019
Pages 139-145