Efficient synthesis of bis(indolyl)methanes catalyzed by (PhCH2PPh3)+Br- under solvent-free conditions
الموضوعات : Iranian Journal of CatalysisFarhad Shirini 1 , Masoumeh Abedini 2 , Manouchehr Mamaghani 3 , Arman Rahmaninia 4
1 - Department of Chemistry, College of Science, University of Guilan, Rasht, zip code 41335, I.R. Iran.
2 - Department of Chemistry, College of Science, University of Guilan, Rasht, zip code 41335, I.R. Iran.
3 - Department of Chemistry, College of Science, University of Guilan, Rasht, zip code 41335, I.R. Iran.
4 - Department of Chemistry, College of Science, University of Guilan, Rasht, zip code 41335, I.R. Iran.
الکلمات المفتاحية: Aldehydes, Solvent-free conditions, Benzyltriphenylphosphonium bromide, Indoles, Bis(indolyl)methanes,
ملخص المقالة :
Benzyltriphenylphosphonium bromide (BTPB) has been applied as an efficient catalyst for the preparation of bis(indolyl)methanes (BIMs) via electrophilic substitution of indoles with aldehydes in the absence of solvent.
[1] T.R. Garbe, M. Kobayashi, N. Shimizu, N.Takesue, M. Ozawa, H. Yukawa, J. Nat. Prod. 63 (2000) 596-598.
[2] M. Karthik, A.K. Tripathi, N.M. Gupta, M. Palanichamy, V. Murugesan, Catal. Commun.5 (2004) 371-375.
[3] M. Auria, Tetrahedron 47 (1991) 9225-9230.
[4] H. Koshima, W. Matzuaka, J. Heterocycl. Chem. 39 (2002) 1089-1092.
[5] B.P. Bandgar, K.A. Shaikh, Tetrahedron Lett. 44 (2003) 1959-1961.
[6] S.J. Ji, S.Y. Wang, Y. Zhang, T.P. Loh, Tetrahedron 60 (2004) 2051-2055.
[7] R. Narajan, P.T. Perumal, Chem. Lett. 3 (2004) 228-232.
[8] C. Ramesh, J. Benerjee, R. Pal, B. Das, Adv. Synth. Catal.345 (2003) 557-559.
[9] Z.H. Zhang, L. Yin, Y.M. Wang, Synthesis (2005) 1949-1955.
[10] A. Chatterjee, S. Manna, J. Benerji, C. Pascard, T. Prangé, J.N. Shoolery, J. Chem. Soc., Perkin Trans. 1 (1980) 553-555.
[11] V.T. Kamble, K.R. Kadam, N.S. Joshi, D.B. Muley, Catal. Commun.8 (2007) 498-502.
[12] H. Firouzabadi, N. Iranpoor, M. Jafarpour, A. Ghaderi, J. Mol. Catal. A: Chem. 253 (2006) 249-251.
[13] H. Firouzabadi, N. Iranpoor, A.A. Jafari, J. Mol. Catal. A: Chem. 244 (2006) 168-172.
[14] N. Azizi, L. Torkian, M.R. Saidi, J. Mol. Catal. A: Chem. 275 (2007) 109-112.
[15] M.M. Hereavi, K. Bakhtiari, A. Fatehi, F.F. Bamoharrami, Catal. Commun.9 (2008) 289-292.
[16] S. Palaniappan, A. John, J. Mol. Catal. A: Chem. 242 (2005) 168-170.
[17] M. Chakrabarty, N. Ghosh, R. Basak, Y. Harigaya, Tetrahedron Lett. 43 (2002) 4075-4078.
[18] G.V.M. Sharma, J.J. Reddy, P.S. Lakshmi, P.R. Krishna, Tetrahedron Lett. 45 (2004) 7729-7732.
[19] M.A. Zolfigol, P. Salehi, M. Shiri, Z. Tanbakouchian, Catal. Common.8 (2007) 173-178.
[20] J.R. Satam, K.D. Parghi, R.V. Jayaram, Catal. Commun.9 (2008) 1071-1078.
[21] W.J. Li, X.F. Lin, J. Wang, G.L. Li, Y.G. Wang, Synth. Commun.35 (2005) 2765-2769.
[22] J.T. Li, H.G. Dai, W.Z. Xu, T.S. Li, Ultrason. Sonochem.13 (2006) 24-27.
[23] K. Tabatabaeian, M. Mamaghani, N. Mahmoodi, A. Khorshidi, Can. J. Chem. 84 (2006) 1541-1545.
[24] D. Chen, L. Yu, P.G. Wang, Tetrahedron Lett. 37 (1996) 4467-4470.
[25] L. Wang, J.H. Han, T.J. Sheng, Z. Fan, X. Tang, Synlett (2005) 337-339.
[26] K. Niknam, M.A. Zolfigol, T. Sadabadi, A. Nejati, J. Iran. Chem. Soc. 3 (2006) 318-322.
[27] F. Shirini, A. Yahyazadeh, M. Abedini, D. ImaniLangroodi, Bull. Korean Chem. Soc. 31 (2010) 1715-1718.
[28] S.R. Mendes, S. Thurow, M.P. Fortes, F. Penteado, E.J. Lenardão, D. Alves, G. Perin, R.G. Jacob, Tetrahedron Lett. 53 (2012) 5402-5406.
[29] A. Hasaninejad, A, Zare, H. Sharghi, K. Niknam, M. Shekouhy, Arkivoc xiv (2007) 39-50.
[30] N. Azizi, E. Gholibeghlo, Z. Manocheri, ScientiaIranica C 19 (2012) 574-578.
[31] R. Tayebee, M.M. Amini, F. Nehzat, O. Sadeghi, M. Armaghan, J. Mol. Catal. A: Chem. 366 (2013) 140-148.
[32] G.D. Gong, J.I. Shun-Jun, J. Zhao-Qin, Z. Min-Feng, L. Teck-Peng, Synlett (2005) 959-962.
[33] H. Hagiwara, M. Sekifuji, T. Hoshi, K. Qiao, C. Yokoyamac, Synlett (2007) 1320-1322.
[34] H. Veisi, S. Hemmati. H. Veisi, J. Chin. Chem. Soc. 56 (2009) 240-245.
[35] S.A. Sadaphal, K.F. Shelke, S.S. Sonar, M.S. Shingare, Cent. Eur. J. Chem. 6 (2008) 622-626.
[36] X.F. Lin, S.L. Cui, Y.G. Wang, Synth. Commun.36 (2006) 3153-3160.
[37] F. Shirini, M. SafarpoorLangroodi, M. Abedini, Chinese Chem. Lett. 21(2010) 1342-1345.
[38] C.J. Magesh, R. Nagarajan, M. Karthink, P.T. Perumal, Appl. Catal. A: General 266 (2004) 1-10.
