K. Singh et al. / Journal of Molecular Catalysis A: Chemical 347 (2011) 34–37
37
3. Conclusion
[10] (a) H. Kurata, H. Nakaminami, K. Matsumoto, T. Kawase, M. Oda, Chem. Com-
mun. (2001) 529;
(b) H. Kurata, K. Haruki, H. Nakaamiami, T. Kawase, M. Oda, Chem. Lett. (2003)
422.
[11] (a) J.R. Majer, Tetrahedron 9 (1960) 106;
In summary, we have demonstrated an efficient condensation
of electron rich heterocycles with a variety of aldehydes using
Amberlyst 15 catalyst, without using solvent in the reaction. The
most attractive feature of this catalytic method is the facile conden-
sation of electron rich heterocycles with aldehydes using justified
stoichiometric quantities. In addition, the Amberlyst 15 catalyzed
protocol is of potential industrial significance as many of the
products obtained herein are of commercial significance besides
the condensation protocol depicted higher yields of the products,
recyclability and environmental friendliness of the catalyst, short
reaction times, and overall practicability of the process as it does not
require any specialized equipment or inert atmospheric conditions.
(b) J.R. Majer, Tetrahedron 9 (1960) 111;
(c) H. Budzikiewicz, H. Eckau, M. Ehrenberg, Tetrahedron Lett. 13 (1972) 3807;
(d) T.J. Novak, D.N. Kramer, H. Klapper, L.W. Daasch, B.L. Murr, J. Org. Chem. 41
(1976) 870.
[12] (a) R. Martinez, A. Espinosa, A. Tarraga, P. Molina, Tetrahedron 64 (2008) 2184;
(b) X. He, S. Hu, K. Liu, Y. Guo, J. Xu, S. Shao, Org. Lett. 8 (2006) 333;
(c) Z. Li, D.S. Guo, H.X. Li, Y. Liu, Chem. J. Chin. Univ. 29 (2008) 2545.
[13] (a) A. Ramirez, S. Garcia-Rubio, Curr. Med. Chem. 10 (2003) 1891;
(b) R.J. Sundberg, The Chemistry of Indole , Academic Press, New York, 1970.
[14] (a) K. Ebitani, K. Nagashima, T. Mizugaki, K. Kaneda, Green Chem. 2 (2000) 157;
(b) M. Onaka, T. Shinoda, Y. Izumi, E. Nolen, Tetrahedron Lett. 34 (1993) 2625.
[15] K. Singh, A. Sharma, Tetrahedron Lett. 48 (2007) 227.
[16] K. Singh, A. Sharma, Tetrahedron 66 (2010) 3682.
[17] K. Singh, A. Sharma, Tetrahedron Lett. 49 (2008) 6234.
[18] (a) E. Choucair, M. Balaz, Eur. J. Org. Chem. (2006) 3007;
(b) K. Shengkai, C.F. Yao, Tetrahedron Lett. 47 (2006) 8827.
[19] C. Srinivas, P.S. Sadhu, S. Palaniappan, J. Heterocycl. Chem. 46 (2009)
997.
Acknowledgements
A Financial assistance (project SR/S1/OC-27/2009) from Depart-
ment of Science and Technology (DST), Government of India, New
Delhi is gratefully acknowledged. SS and AS thanks UGC and CSIR,
New Delhi for Research Fellowships.
[20] P.A. Tempera, R.D. Colinas, Bravo, Tetrahedron Lett. 51 (2010) 5372.
[21] (a) J.R. Caycho, F.G. Tellado, P.D. Armas, J.J.M. Tellado, Tetrahedron Lett. 38
(1997) 227;
(b) Y.H. Liu, Q.S. Liu, Z.H. Liu, Z.H. Zhang, J. Mol. Catal. A: Chem. 296 (2008) 42;
(c) M. Tazbaksh, R. Hossseinzadeh, Z. Lasemi, Synlett 4 (2004) 635;
(d) K.S. Kumar, J. Iqbal, M. Pal, Tetrahedron Lett. 50 (2009) 6244;
(e) J.S. Yadav, B.V.S. Reddy, P. Vishnumurthy, Tetrahedron Lett. 49 (2008) 4498.
[22] R. Naik, P. Joshi, S.P. Kaiwar, R.K. Deshpande, Tetrahedron 59 (2003) 2207.
[23] H. Maeda, A. Osuka, Y. Hisaeda, H. Furuta, Org. Lett. 5 (2003) 1293.
[24] B. Ke, Y. Qin, Y. Wang, F. Wang, Synth. Commun. 35 (2005) 1209.
[25] (a) A. Sharon, P.R. Maulik, V.J. Ram, Tetrahedron Lett. 45 (2004) 5099;
(b) S.M.S. Chauhan, B. Garg, T. Bisht, Molecules 12 (2007) 2458.
[26] L. Zeng, E.W. Miller, A. Pralle, E.Y. Isacoff, C.J. Chang, J. Am. Ceram. Soc. 128
(2006) 10.
Appendix A. Supplementary data
Supplementary data associated with this article can be found, in
References
[27] A. Burrell, D.L. Officer, P.G. Plieger, D.C.W. Reid, Chem. Rev. 101 (2001) 2751.
[28] K. Singh, S. Behal, M.S. Hundal, Tetrahedron 61 (2005) 6614.
[29] A.F. Oleinik, E.N. Dozorova, N.P. Soloveva, L.M. Polukhina, L.N. Filitis, O.N.
Polyakova, G.N. Pershin, Kim. -Farm. Zh. 17 (1983) 928.
[30] (a) S. Tanaka, H. Tomokuni, J. Heterocycl. Chem. 28 (1991) 991;
(b) W.-S. Cho, C.-H. Lee, Bull. Korean Chem. Soc. 19 (1998) 314;
(c) W.H. Brown, H. Sawatzky, Can. J. Chem. 34 (1956) 1147.
[31] (a) E. Fahy, B.C.M. Potts, D.J. Faulkner, K. Smith, J. Nat. Prod. 54 (1991) 564;
(b) T. Irie, K. Kubushirs, K. Suzuki, K. Tsukazaki, K. Umezawa, S. Nozawa, Anti-
cancer Res. 31 (1999) 3061;
[1] K.M. Kadish, K.M. Smith, R. Guilard, The Porphyrin Handbook, 1–2, Academic
Press, New York, 2000, and references therein.
[2] (a) E. Vogel, Pure Appl. Chem. 62 (1990) 557;
(b) E. Vogel, N. Lux, J. Dorr, T. Pelster, T. Berg, H.-S. Bohm, F. Behrens, J. Lex, D.
Bremm, G. Hohlneicher, Angew. Chem. Int. Ed. 39 (2000) 1101;
(c) J.L. Sessler, D. Seidel, Angew. Chem. Int. Ed. 42 (2003) 5134.
[3] (a) R.M. Musau, A. Whiting, J. Chem. Soc. Perkin Trans. 1 (1994) 2881;
(b) K. Goto, Top. Heterocycl. Chem. 17 (2008) 97.
[4] (a) V.K. Gupta, M.K. Pal, A.K. Singh, Talanta 79 (2009) 528;
(b) T. Sone, Y. Ohba, R. Watanabe, Bull. Chem. Soc. Jpn. 62 (1989) 1346;
(c) J.M. Baker, Adv. Heterocycl. Chem. 32 (1982) 83;
(d) Z. Hu, J.L. Atwood, M.P. Cava, J. Org. Chem. 59 (1994) 8071;
(e) J.S. Reddy, V.G. Anand, Chem. Commun. (2008) 1326.
[5] (a) J. Zheng, R. Wen, X. Luo, G. Lin, J. Zhang, L. Xu, L. Guo, H. Jiang, Bioorg. Med.
Chem. Lett. 16 (2006) 225;
(c) J.T. Kuette, Chimica 60 (2006) 543.
[32] (a) F. Amat-guerri, R. Martinez-utrilla, C. Pascual, J. Chem. Res. (M) (1984) 1578;
(b) J. Banerji, A. Chatterjiee, S. Manna, C. Pascard, T. Prange, J. Shoolery, Hete-
rocycles 15 (1981) 325;
(c) A. Chatterjee, S. Manna, T. Benerji, J. Shoolery, J. Chem. Soc. Perkin I (1980)
553.
(b) S. Sasaki, N. Ishibashi, T. Kuwamura, H. Sano, M. Matoba, T. Nisikawa, M.
Maeda, Bioorg. Med. Chem. Lett. 8 (1998) 2983;
[33] M. Shiri, M.A. Zolfigol, H. Gerhardus, Z. Tanbakouchian, Chem. Rev. 110 (2010)
2250.
(c) G.H. Fulep, C.E. Hoesl, G. Hofner, K.T. Wanner, Eur. J. Med. Chem. 41 (2006)
809.
[6] (a) T. Zhao, Z. Wei, Y. Song, W. Xu, W. Hu, D. Zhu, J. Mater. Chem. 17 (2007)
4377;
(b) K.J. Hoffmann, E.J. Samuelsen, P.H.J. Carlsen, Synth. Met. 113 (2000) 161;
(c) T. Benincori, S. Rizzio, F. Sannicolo, Macromolecules 36 (2003) 5114.
[7] A.R. Katritzky, L. Xie, W.-Q. Fan, J. Org. Chem. 58 (1993) 4376.
[8] (a) T.W. Green, G.M. Wuts, Protective Groups in Organic Synthesis , 3rd ed.,
Wiely, New York, 1999;
[34] R. Chimmani, J. Banerjee, R. Pal, B. Das, Adv. Synth. Catal. 345 (2003) 557.
[35] (a) M.S. Shchepinov, V.A. Korshun, Chem. Soc. Rev. 32 (2003) 170;
(b) D.F. Duxbury, Chem. Rev. 93 (1993) 381;
(c) R.J. Schnitzer, F. Hawking, Experimental Chemotherapy, vol. 1, Academic
Press, New York, 1963.
[36] (a) A. McDougal, M.S. Gupta, D. Morrow, K. Ramamoorthy, J.E. Lee, S.H. Safe,
Breast Cancer Res. Treat. 66 (2001) 147;
(b) A. McDougal, M. Sethi-Gupta, K. Ramamoorthy, G. Sun, S. Safe, Cancer Lett.
151 (2000) 169.
(b) D.A. Stetsenko, E.N. Lubyako, V.K. Potapov, T.L. Azhikima, E.D. Sverdlov,
Tetrahedron Lett. 37 (1996) 3571.
[37] M. Kobayashi, S. Aoki, K. Gato, K. Matsunami, M. Kurosu, I. Kitagawa, Chem.
Pharm. Bull. 42 (1994) 2449.
[9] (a) F. Cherioux, L. Guyard, P. Audebert, Adv. Mater. 10 (1998) 1013;
(b) S. Brasselet, F. Cherioux, P. Audebert, J. Zyss, Chem. Mater. 11 (1999) 1915.
[38] D. Kim, A. Osuka, Acc. Chem. Res. 37 (2004) 735.
[39] V. Nair, K.G. Abhilash, N. Vidya, Org. Lett. 7 (2005) 5857.