Iranian chemical communication

Current Issue

By Issue

By Author

By Subject

Author Index

Keyword Index

About Journal

Aims and Scope

Editorial Board

Publication Ethics

Indexing and Abstracting

Related Links

FAQ

Peer Review Process

Journal Metrics

News

A novel and efficient synthesis of bisindolyl methanes with using silica-supported 3-(triethoxysilyl) propane-1-ammonium chloride as reusable catalyst under solvent free conditions

Document Type : Original Research Article

Authors

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

2 Department of Chemistry, Payame Noor University, P.O. Box 19395-3697, Tehran, Iran

Abstract

A facile and efficient synthesis of bis(indolyl)methanes derivatives (3a-u) was reported via a condensation reaction of aldehydes and indole in the presence of by silica-supported-3-(triethoxysilyl) propane-1-ammonium chloride catalysis under solvent free conditions. We studied the reaction in different conditions and optimized. The use of just 0.02 g of (silica gel-ammonium salt) is sufficient. The reaction was carried out at 110 °C under thermal condition. This method, including some advantages such as mild reaction condition, easy work-up, and recoverable and reusable catalyst.
A facile and efficient synthesis of bis(indolyl)methanes derivatives (3a-u) was reported via a condensation reaction of aldehydes and indole in the presence of by silica-supported-3-(triethoxysilyl) propane-1-ammonium chloride catalysis under solvent free conditions. We studied the reaction in different conditions and optimized. The use of just 0.02 g of (silica gel-ammonium salt) is sufficient. The reaction was carried out at 110 °C under thermal condition. This method, including some advantages such as mild reaction condition, easy work-up, and recoverable and reusable catalyst..

Graphical Abstract

A novel and efficient synthesis of bisindolyl methanes with using silica-supported 3-(triethoxysilyl) propane-1-ammonium chloride as reusable catalyst under solvent free conditions

Keywords

Main Subjects

References
[1] A. Domling, I. Ugi, Angw. Chemie Inter. Ed., 2000, 39(18), 3168-3210.
[2] S.A. Morris, R.J. Andersen, Tetrahedron, 1990, 46, 715-720.
[3] G. Bifulco, I. Bruno, R. Riccio, J. Lavayre, G. Bourdy, J. Nat. Prod., 1995, 58, 1254-1260.
[4] M.A. Zeligs, J. Med. Food, 1998, 1 (2), 67-82.
[5] X. Ge, S. Yannai, G. Rennert, N. Gruener, F.A. Gares, Biochem. Biophys. Res. Commun., 1996, 28, 153-157.
[6] M. Chakrabarty, R. Basak, Y. A. Harigaya, Heterocycles, 2001, 55, 2431–2447.
[7] M. Roomi, S. MacDonald, Can. J. Chem., 1970, 48,139-143.
[8] R. Nagarajan, P. T. Perumal, Tetrahedron, 2002, 58, 1229-1232.
[9] J.S. Yadav, B.V. S. Reddy, C.V.S. R. Murthy, G.M. Kumar, C. Madan, Synthesis, 2001, 783–787.
[10] G. Babu, N. Sridhar, P.T. Perumal, Synth. Commun., 2000, 30, 1609–1614.
[11] R. Nagarajan, P.T. Perumal, Chem. Lett., 2004, 33, 288–289.
[12] L.-P. Mo, Z.-C. Ma, and Z.-H. Zhang,Synthetic Commun., 2004, 35, 1997–2005.
[13] B.P. Bandgar, K.A. Shaikh, J. Chem. Res. Synop., 2004, 34–36.
[14] X.-L. Mi, S.-Z. Luo, J.-Q. He, J.-P. Cheng, Tetrahedron Lett., 2004, 45, 4567–4570.
[15] D. Chen, L.Yu, P.G. Wang, Tetrahedron Lett.,1996, 37, 4467–4470.
[16] M. Xia, S.-B. Wang, W.-B. Yuan, Synth. Commun., 2004, 34, 3175–3182.
[17] (a) S.-J. Ji, S.-Y. Wang, Y. Zhang, T.-P. Loh, Tetrahedron, 2004, 60, 2051–2055; (b) B.P. Bandgar, K.A. Shaikh, Tetrahedron Lett., 2003, 44, 1959–1961.
[18] H. Koshima, W. Matsuaka, J. Heterocycl. Chem., 2002, 39, 1089–1091.
[19] R. Nagarajan, P.T. Perumal, Chem. Lett., 2004, 33, 288–289.
[20] C. Ramesh, J. Baneree, R. Pal, B. Das, Adv. Synth. Catal., 2003, 345, 557–559.
[21] R. Nagarajan, P.T. Perumal, Synth. Commun., 2002, 32, 105–109.
[22] C. Ramesh, N. Ravindranath, B. Das, J. Chem. Res. Synop., 2003, 72–74.
[23] (a) M. Karthik, A.K. Tripathi, N.M. Gupta, M. Palanichamy, V. Murugesan, Catal. Commn., 2004, 5, 371–375; (b) A.V. Reddy, K. Ravinder, V.L.N.  Reddy, T.V. Goud, V. Ravikanth, Y. Venkateseswarlu, Synth. Commun., 2003, 33, 3687–3694.
[24] (a) M. Chakrabarty, N. Gosh, R. Basak, Y. Harigaya, Tetrahedron Lett., 2002, 43, 4075–4078; (b) G. Penieres-Carrillo, J.G. Garcı´a-Estrada, J.L. Gutie´rrez-Ramı´rez, C. Alvarez-Toledano, Green Chem., 2003, 5, 337–339.
[25] M.A. Zolfigol, P. Salehi, M. Shirl, Phosphorus, Sulfur Silicon Relat. Elem., 2004, 179, 2273–2277.
[26] G.V.M. Sharma, J.J. Reddy, P.S. Lakshmi, P.R. Krishna, Tetrahedron Lett., 2004, 45, 7729–7732.
[27] J.S. Yadav, B.V.S. Reddy, S. Sunitha, Adv. Synth. Catal., 2003, 345, 349–352.
[28] X.-L. Feng, C.-J. Guan, C.-X. Zhao, Synth. Commun., 2004, 34, 487–492.
[29] S.-J. Ji, M.-F. Zhou, D.-G. Gu, S.-Y. Wang, T.-P. Loh, Synlett, 2003, 2077_2079.
[30] R. Ranjbar-Karimi, A. KhajehKhezri, M. Anary-Abbasinejad, Het. Lett., 2014, 4, 2, 301-310.
[31] R.R. Nagawade, D.B. Shinde, Bull. Korean Chem. Soc., 2005, 26, 12, 1962-1964.
[32] M. Xia, S.B. Wang, W.B. Yuan, Synth. Commun., 2004, 34, 3175-3182.
[33] S.X. Wang, J.T. Li, L.I. Geng, J. Chem. Res. Synop., 2003, 370-373.
[34] A. Ahad, M. Farooqui, P.M. Arifkhan, M. Farooqui, Int. J. Green Chem. Bioproc., 2012, 2, 4, 31-33.
[35] R.R. Nagawade, D.B. Shinde, ActaChemie, Slov., 2006, 53, 210-213.
[36] Z. Ji-ming, X. Rui-ping, T. Yan, Z. Jian-hua, Chem. Res. Chinese Uni., 2009, 25, 6, 941-944.
[37] (a) A. Hasaninejad, A. Zare, H. Sharghi, K. Niknam, M. Shekouhy, Arkivoc, 2007, xiv, 39-50; (b) A. Azizi, E. Gholibeghlo, Z. Manocheri, ScienticaIranica, 2012, 19, 574-578; (c) H. Firouzabadi, N. Iranpoor, H. Jafarpour, A. Ghaderi, J. Mol. Catal. A: Chem., 2006, 253, 249-251.
[38] B.P. Bandgar, A.V. Patil, V.T. Kamble, Arkivoc, 2007, xiv, 252-258.
[39] D.M. Pore, U.V. Desai, T.S. Thopate, P.P. Wadgaonkar, Arkivoc, 2006, 12, 75-80.
[40] J. Banothv, R. Gali, R. Velpula, R. Bavantula, P.A. Grooks, ISRN Org. Chem. Article ID 616932, 2013, 5 Pages.
Iranian chemical communication
Volume 4, Issue 4, pp. 359-490, Serial No. 13
October 2016
Pages 433-448
Files
Share
How to cite
Statistics