Poly(4-vinylpyridinium) perchlorate as an efficient and recyclable catalyst for the synthesis of biscoumarins and bisindoles

doi:10.1016/S1872-2067(14)60061-9

Abstract

Abstract:

Poly(4-vinylpyridinium) perchlorate has been used as an efficient solid acid catalyst for the synthesis of 3,3'-(arylmethylene)bis(4-hydroxycoumarins) and bis(indolyl)methanes, with the products being formed in excellent yields over very short reaction times under mild and environmentally friendly conditions. This catalyst can be reused several times without any appreciable loss in its activity.

Key words: Poly(4-vinylpyridinium) perchlorate, Biscoumarins, Bis(indolyl)methanes, Reusable catalyst

Farhad Shirini, Saeed Esmaeeli-Ranjbar, Mohadeseh Seddighi. Poly(4-vinylpyridinium) perchlorate as an efficient and recyclable catalyst for the synthesis of biscoumarins and bisindoles[J]. Chinese Journal of Catalysis, 2014, 35(7): 1017-1023.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(14)60061-9

https://www.cjcatal.com/EN/Y2014/V35/I7/1017

References

[1] Tamami B, Borujeni K P. Iran Polym J, 2009, 18: 191
[2] Herrman W A, Kratzer R M, Blümel J, Friedrich H B, Fischer R W, Apperley D C, Mink J, Berkesi O. J Mol Catal A, 1997, 120: 197
[3] Tamami B, Hatam M, Mohadjer D. Polymer, 1991, 32: 2666
[4] Albadi J, Keshavarz M, Shirini F, Vafaie-nezhad M. Catal Commun, 2012, 27: 17
[5] Khaligh N G, Shirini F. J Mol Catal A, 2011, 348: 20
[6] Kong Y, Fu Y J, Zu Y G, Chang F R, Chen Y H, Liu X L, Stelten J, Schiebel H M. Food Chem, 2010, 121: 1150
[7] Zhou P, Takaishi Y, Duan H, Chen B, Honda G, Itoh M, Takeda Y, Kodzhimatov O K, Lee K H. Phytochemistry, 2000, 53: 689
[8] Neyts J, De Clercq E, Singha R, Chang Y H, Das A R, Chakraborty S K, Hong S C, Tsay S C, Hsu M H, Hwu J R. J Med Chem, 2009, 52: 1486
[9] Ito C, Itoigawa M, Onoda S, Hosokawa A, Ruangrungsi N, Okuda T, Tokuda H, Nishino H, Furukawa H. Phytochemistry, 2005, 66: 567
[10] Bhattacharyya S S, Paul S, Mandal S K, Banerjee A, Boujedaini N, Khuda-Bukhsh A R. Eur J Pharmacol, 2009, 614: 128
[11] Hussain H, Hussain J, Al-Harrasi A, Krohn K. Tetrahedron, 2012, 68: 2553
[12] Manolov I, Maichle-Moessmer C, Danchev N. Eur J Med Chem, 2006, 41: 882
[13] Khan K M, Iqbal S, Lodhi M A, Maharvi G M, Ullah Z, Choudhary M I, Rahman A, Perveen S. Bioorg Med Chem, 2004, 12: 1963
[14] Kidwai M, Bansal V, Mothsra P, Saxena S, Somvanshi R K, Dey S, Singh T P. J Mol Catal A, 2007, 268: 76
[15] Khurana J M, Kumar S. Tetrahedron Lett, 2009, 50: 4125
[16] Mehrabi H, Abusaidi H. J Iran Chem Soc, 2010, 7: 890
[17] Tavakoli-Hoseini N, Heravi M M, Bamoharram F F, Davoodnia A, Ghassemzadeh M. J Mol Liq, 2011, 163: 122
[18] Tabatabaeian K, Heidari H, Khorshidi A, Mamaghani M, Mahmoodi N O. J Serb Chem Soc, 2012, 77: 407
[19] Das Gupta A, Samanta S, Mondal R, Mallik A K. Bull Korean Chem Soc, 2012, 33: 4239
[20] Niknam K, Jamali A. Chin J Catal (催化学报), 2012, 33: 1840
[21] Sharma V, Kumar P, Pathak D. J Heterocyclic Chem, 2010, 47: 491
[22] Diana P, Carbone A, Barraja P, Martorana A, Gia O, DallaVia L, Cirrincione G. Bioorg Med Chem Lett, 2007, 17: 6134
[23] Bharate S B, Bharate J B, Khan S I, Tekwani B L, Jacob M R, Mudududdla R, Yadav R R, Singh B, Sharma P R, Maity S, Singh B, Khan I A, Vishwakarma R A. Eur J Med Chem, 2013, 63: 435
[24] Sashidhara K V, Kumar A, Kumar M, Srivastava A, Puri A. Bioorg Med Chem Lett, 2010, 20: 6504
[25] Kamal A, Srikanth Y V V, Ramaiah M J, Khan M N A, Reddy M K, Ashraf M, Lavanya A, Pushpavalli S N C V L, Pal-Bhadra M. Bioorg Med Chem Lett, 2012, 22: 571
[26] Xu H Y, Zi Y, Xu X P, Wang S Y, Ji S J. Tetrahedron, 2013, 69: 1600
[27] Ke B, Qin Y, He Q F, Huang Z Y, Wang F P. Tetrahedron Lett, 2005, 46: 1751
[28] Zeng X F, Ji S J, Wang S Y. Tetrahedron, 2005, 61: 10235
[29] Ji S J, Wang S J, Zhang Y, Loh T P. Tetrahedron, 2004, 60: 2051
[30] An L T, Ding F Q, Zou J P, Lu X H, Zhang L L. Chin J Chem, 2007, 25: 822
[31] Shirini F, Langroodi M S, Abedini M. Chin Chem Lett, 2010, 21: 1342
[32] Wang S Y, Ji S J. Tetrahedron, 2006, 62: 1527
[33] Gu D G, Ji S J, Jiang Z Q, Zhou M F, Loh T P. Synlett, 2005: 959
[34] Jafarpour M, Rezaeifard A, Golshani T. J Heterocyclic Chem, 2009, 46: 535
[35] Mishra S, Ghosh R. Indian J Chem B, 2011, 50B: 1630
[36] Hasaninejad A, Shekouhy M, Zare A, Ghattali S M S H, Golzar N. J Iran Chem Soc, 2011, 8: 411
[37] Shirini F, Khaligh N G. Chin J Catal (催化学报), 2013, 34: 1890
[38] Shirini F, Mamaghani M, Seddighi M. Catal Commun, 2013, 36: 31
[39] Shirini F, Jolodar O G. J Mol Catal A, 2012, 356: 61
[40] Shirini F, Akbari-Dadamahaleh S, Mohammad-Khah A. C R Chim, 2013, 16: 945
[41] Khaligh N G. J Mol Catal A, 2012, 363: 90
[42] Manolov I, Maichle-Moessmer C, Nicolova I, Danchev N. Arch Pharm Chem Life Sci, 2006, 339: 319
[43] Rekha M, Manjunath H R, Nagaraju N. J Ind Eng Chem, 2013, 19: 337
[44] Nagawade R R, Shinde D B. Acta Chim Slov, 2006, 53: 210