Document Type : Original Research Article


Department of Organic Chemistry, Faculty of Sciences, University of Guilan, Rasht, Iran


A simple, efficient and convenient route is described for the synthesis of bis-indolyl methanes by using recyclable catalyst sulfonylbis(1,4phenylene)bissulfamic acid (SPSA). In this procedure, we synthesize a bis-indolyl methane derivative via the three component reactions of two equivalent indoles with one equivalent of various aromatic aldehydes in the presence of 10 mol% SBSA as a heterogeneous catalyst under solvent-free conditions at 110 °C for the convinced reaction times (30–60 min). The advantages of this protocol towards the synthesis of bis-indolyl methane derivatives are: I) use of solvent-free conditions, II) inexpensive catalyst, III) using commercially available precursors, d) reusability of SBSA up to several cycles without much loss in reactivity, IV) simple work-up, V) high yields of pure products, VI) short reaction times. The structure of all bis(indolyl)methane derivatives were confirmed by melting point, FT-IR, 1H NMR spectra and were compared with reliable references.

Graphical Abstract

Sulfonylbis(1,4-phenylene)bissulfamic acid (SPSA): Introduction of an efficient and reusable catalyst for the synthesis of bis(indolyl)methanes


Main Subjects

[1]. Armstrong R.W., Combs A.P., Tempest P.A., Brown S.D., Keating T.A. Acc. Chem. Res., 1996, 29:123
[2]. Ibrahim Y.A., Behbehani H., Ibrahim M.R. Tetrahedron Lett., 2002, 43:4207
[3]. Tabrizian E., Amoozadeh A., Rahmani S., Imanifar E., Azhari S., Malmir M. Chin. Chem. Lett., 2015, 26:1278
[4]. Khaksar S., Tajbakhsh M., Gholami M. C. R. Chimie., 2014, 17:30
[5]. Saeidian H., Moradnia F. Iran. Chem. Commun., 2017, 5:252
[6]. Kale S.R., Kahandal S.S., Burange A.S., Gawande M.B., Jayaram R.V. Catal. Sci. Technol., 2013, 3:2050
[7]. Mahmoodi, N.O., Khazaei Z., Zeydi M.M. J. Iran. Chem. Soc., 2017, 4:1889
[8]. Endo T., Tsuda M., Fromont J., Kobayashi J., Hyrtinadine A. J. Nat. Prod., 2007, 70:423
[9]. Kalla R.M.N., Khalivulla S.I., Rasheed S., Fakurazi S., Arulselvan P., Lasekan O., Abas F. Int. J. Mol. Sci., 2013, 14:1843
[10]. Kamal A., Khan M.N.A., Reddy K.S., Srikanth Y.V.V., Ahmed S.K., Kumar K.P., Murthy U.S.N. J. Enzyme. Inhib. Med. Chem., 2009, 24:559
[11]. Benabadji S.H., Wen R., Zheng J., Dong X., Yuan S. Acta. Pharmacol. Sinica., 2004, 25:666
[12]. Sujatha K., Perumal P.T., Muralidharan D., Rajendran M. Indian J. Chem., 2009, 48:267
[13]. Karthik M., Tripathi A.K., Gupta N.M., Palanichamy M., Murugesan V. Catal. Commun., 2004, 5:371
[14]. Pore D.M., Desai U.V., Thopate T.S., Wadgaonkar P.P. Arkivoc, 2006, 12:75
[15]. Lin X.F., Cui S.L., Wang Y.G. Synth. Commun., 2006, 36:3153
[16]. Niknam K., Zolfigol M.A., Sadabadi T., Nejati A. J. Iran. Chem. Soc., 2006, 3:318
[17]. Reddy B.M., Sreekanth P.M., Lakshmanan P. J. Mol. Catal. A Chem., 2005, 237:93
[18]. Maiti A.K., Bhattacharyya P. J. Chem. Res., 1997, s:424
[19]. Deb M.L., Bhuyan P.J. Tetrahedron Lett., 2006, 47:1441
[20]. Sharma G.V.M., Reddy J.J., Lakshmi P.S., Krishna P.R. Tetrahedron Lett., 2004, 45:7729
[21]. Karthik M., Tripathi A.K., Gupta N.M., Palanichamy M., Murugesan V. Catal Commun., 2004, 5:371
[22]. Firouzabadi H., Iranpoor N., Jafari A.A. J. Mol. Catal. A Chem., 2005, 244:168
[23]. Pradhan P.K., Dey S., Giri V.S., Jaisankar P. Synthesis, 2005, 37:1779
[24]. Azizi N., Torkian L., Saidi M.R. J. Mol. Catal. A Chem., 2007, 275:109
[25]. Hosseini-Sarvari M. Acta Chim. Slovenica, 2007, 54:354
[26]. Mehrazma S., Azizi N., Saidi M.R. Lett. Org. Chem., 2006, 3:161
[27]. Firouzabadi H., Iranpoor N., Jafarpour M., Ghaderi A. J. Mol. Catal. A Chem., 2006, 253:249
[28]. Kamble V.T., Bandgar B.P., Bavikar S.N. Chin. J. Chem., 2007, 25;13
[29]. Kamble V.T., Kadam K.R., Joshi N.S., Muley D.B. Catal. Commun., 2007, 8:498
[30]. Koshima H., Matsuaka W. J. Heterocycl. Chem., 2002, 39:1089
[31]. Khodaei M.M., Mohammadpoor-Baltork I., Memarian H.R., Khosropour A.R., Nikofar K., Ghanbary P. J. Heterocycl. Chem., 2008, 45:1
[32]. Ghorbani-Vaghei R., Veisi H., Keypour H., Dehghani-Firouzabadi A. A. Mol. Divers, 2010, 14:87
[33]. Shirini F., Yahyazadeh A., Abedini M., Imani Langroodi D. Bull. Korean Chem. Soc., 2010, 31: 1715
[34]. Rekha M., Manjunath H.R., Nagaraju N. J. Indust. Engin. Chem., 2013, 19:337
[35]. Azizi N., Gholibeghlo E., Manocheri Z. ScientiaIranica C, 2012, 19:574
[36]. Jhansi Rani V., Veena Vani K., Venkata Rao C. Synth. Commun., 2012, 42:2048
[37]. Shirini F., Safarpoor Langroodi M., Abedini M. Chin. Chem. Lett., 2010, 21:1342
[38]. Hasaninejad A., Zare A., Sharghi H., Niknam K., Shekouhy M. Arkivoc, 2007, xiv:39
[39]. Gong G.D., Shun-Jun J.I., Zhao-Qin J., Min-Feng Z., Teck-Peng L. Synlett, 2005, 959
[40]. Hagiwara H., Sekifuji M., Hoshi T., Qiao K., Yokoyamac C. Synlett, 2007, 1320
[41]. Magesh C.J., Nagarajan R., Karthink M., Perumal P.T. Appl. Catal. A: General, 2004, 266:1