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Polyethylene Gylcol (PEG-400) as an Efficient and Recyclable Reaction Medium for One-Pot Three-Component Synthesis of Imidazo[1,2-a]pyridine Derivatives
Corresponding Author(s) : K. Bhaskar
Asian Journal of Chemistry,
Vol. 28 No. 11 (2016): Vol 28 Issue 11
Abstract
Polyethylene glycol (PEG) was found to be an inexpensive nontoxic and effective medium for the one-pot three-component synthesis of imidazo[1,2-a]pyridine derivatives under catalyst-free conditions in excellent yields. Environmental acceptability, low cost, high yields and recyclability of the polyethylene glycol are the important features of this protocol.
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- H. Yan, Y. Wang, C. Pan, H. Zhang, S. Yang, X. Ren, J. Li and G. Huang, Eur. J. Org. Chem., 2754 (2014); doi:10.1002/ejoc.201301658
References
J.P. Michael, Nat. Prod. Rep., 16, 675 (1999); doi:10.1039/a809404g.
(a) T. Biftu, D. Feng, M. Fisher, G.-B. Liang, X. Qian, A. Scribner, R. Dennis, S. Lee, P.A. Liberator, C. Brown, A. Gurnett, P.S. Leavitt, D. Thompson, J. Mathew, A. Misura, S. Samaras, T. Tamas, J.F. Sina, K.A. McNulty, C.G. McKnight, D.M. Schmatz and M. Wyvratt, Bioorg. Med. Chem. Lett., 16, 2479 (2006); doi:10.1016/j.bmcl.2006.01.092; (b) A. Scribner, R. Dennis, S. Lee, G. Ouvry, D. Perrey, M. Fisher, M. Wyvratt, P. Leavitt, P. Liberator, A. Gurnett, C. Brown, J. Mathew, D. Thompson, D. Schmatz and T. Biftu, Eur. J. Med. Chem., 43, 1123 (2008); doi:10.1016/j.ejmech.2007.09.013.
K.S. Gudmundsson and B.A. Johns, Bioorg. Med. Chem. Lett., 17, 2735 (2007); doi:10.1016/j.bmcl.2007.02.079.
C. Enguehard-Gueiffier, F. Fauvelle, J.C. Debouzy, A. Peinnequin, I. Thery, V. Dabouis and A. Gueiffier, Eur. J. Pharm. Sci., 24, 219 (2005); doi:10.1016/j.ejps.2004.10.009.
A.S. Howard, in eds.: A.R. Katritzky, C.W. Rees and E.V.F. Scriven, In Comprehensive Heterocyclic Chemistry II; Pergamon Press: London, Chap. 10, p. 262 (1996).
F. Couty and G. Evano, in eds.: A.R. Katritzky, C.A. Ramsden, E.V.F. Scriven and R.J.K. Taylor, In Comprehensive Heterocyclic Chemistry III; Elsevier Science: Oxford, vol. 11, Chap. 11, p. 409 (2008).
R. Gompper, H.J. Mair and K. Polborn, Synthesis, 696 (1997); doi:10.1055/s-1997-1405; T. Kanbara, T. Kushida, N. Saito, I. Kuwajima, K. Kubota and T. Yamamoto, Chem. Lett., 583 (1992); doi:10.1246/cl.1992.583.
G.S. Hanan, D. Volkmer, U.S. Schubert, J.-M. Lehn, G. Baum and D. Fenske, Angew. Chem. Int. Ed. Engl., 36, 1842 (1997); doi:10.1002/anie.199718421; A. Semenov, J.P. Spatz, M. Möller, J.-M. Lehn, B. Sell, D. Schubert, C.H. Weidl and U.S. Schubert, Angew. Chem. Int. Ed., 38, 2547 (1999); doi:10.1002/(SICI)1521-3773(19990903)38:17<2547::AID-ANIE2547>3.0.CO;2-M.
A.S. Howard, in eds.: A.R. Katritzky, C.W. Rees and E.V.F. Scriven, In Comprehensive Heterocyclic Chemistry II; Pergamon Press: London, vol. 8 Chap. 10, pp 262 (1996).
R. Goel, V. Luxami and K. Paul, RSC Adv., 5, 81608 (2015); doi:10.1039/C5RA14795F.
C. Blackburn, B. Guan, P. Fleming, K. Shiosaki and S. Tsai, Tetrahedron Lett., 39, 3635 (1998); doi:10.1016/s0040-4039(98)00653-4.
C. Roubaud, P. Vanelle, J. Maldonado and M.P. Crozet, Tetrahedron, 51, 9643 (1995); doi:10.1016/0040-4020(95)00539-K.
A. Kiselyov, Tetrahedron Lett., 46, 4487 (2005); doi:10.1016/j.tetlet.2005.04.124.
N.W. Bristow, P.T. Charlton, D.A. Peak and W.F. Short, J. Chem. Soc., 616 (1954); doi:10.1039/JR9540000616.
A.R. Katritzky, Y.-J. Xu and H. Tu, J. Org. Chem., 68, 4935 (2003); doi:10.1021/jo026797p.
(a) A. Dömling, Chem. Rev., 106, 17 (2006); doi:10.1021/cr0505728; (b) A. Dömling and I. Ugi, Angew. Chem. Int. Ed., 39, 3168 (2000); doi:10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U.
I. Ugi and R. Meyr, Chem. Ber., 94, 2229 (1961); doi:10.1002/cber.19610940844.
C. Blackburn, Tetrahedron Lett., 39, 5469 (1998); doi:10.1016/S0040-4039(98)01113-7.
H. Bienaymé and K. Bouzid, Angew. Chem. Int. Ed., 37, 2234 (1998); doi:10.1002/(SICI)1521-3773(19980904)37:16<2234::AID-ANIE2234>3.0.CO;2-R.
K. Groebke, L. Weber and F. Mehlin, Synlett, 1998, 661 (1998); doi:10.1055/s-1998-1721.
R.S. Varma and D. Kumar, Tetrahedron Lett., 40, 7665 (1999); doi:10.1016/S0040-4039(99)01585-3.
S.M. Ireland, H. Tye and M. Whittaker, Tetrahedron Lett., 44, 4369 (2003); doi:10.1016/S0040-4039(03)00941-9.
V.Z. Parchinsky, O. Shuvalova, O. Ushakova, D.V. Kravchenko and M. Krasavin, Tetrahedron Lett., 47, 947 (2006); doi:10.1016/j.tetlet.2005.11.152.
A. Shaabani, E. Soleimani and A. Maleki, Tetrahedron Lett., 47, 3031 (2006); doi:10.1016/j.tetlet.2006.03.011.
(a) L.R. Odell, M.T. Nilsson, J. Gising, O. Lagerlund, D. Muthas, A. Nordqvist, A. Karlen and M. Larhed, Bioorg. Med. Chem. Lett., 19, 4790 (2009); doi:10.1016/j.bmcl.2009.06.045; (b) M.C. Pirrung, S. Ghorai and T.R. Ibarra-Rivera, J. Org. Chem., 74, 4110 (2009); doi:10.1021/jo900414n; (c) S.K. Guchhait and C. Madaan, Synlett, 628 (2009); doi:10.1055/s-0028-1087915; (d) M. Nayak, S. Batra and S. Kanojiya, Synthesis, 431 (2009); doi:10.1055/s-0028-1083306; (e) A. Shaabani, E. Soleimani, A. Maleki and J. Moghimi-Rad, Synth. Commun., 38, 1090 (2008); doi:10.1080/00397910701862931; (f) F. Mert-Balci, J. Conrad, U. Beifuss, K. Meindl, T. Schulz and D. Stalke, Synthesis, 3649 (2008); doi:10.1055/s-0028-1083602; (g) A.L. Rousseau, P. Matlaba and C.J. Parkinson, Tetrahedron Lett., 48, 4079 (2007); doi:10.1016/j.tetlet.2007.04.008; (h) A. Shaabani, A. Maleki, J. Moghimi Rad and E. Soleimani, Chem. Pharm. Bull. (Tokyo), 55, 957 (2007); doi:10.1248/cpb.55.957; (i) V.G. Nenajdenko, A. Reznichenko, L. Balenkova and E.S. Russ, Chem. Bull, 56, 560 (2007); doi:10.1007/s11172-007-0093-1.
L. Nagarapu, R. Mallepalli, L. Yeramanchi and R. Bantu, Tetrahedron Lett., 52, 3401 (2011); doi:10.1016/j.tetlet.2011.04.095.
H. Yan, Y. Wang, C. Pan, H. Zhang, S. Yang, X. Ren, J. Li and G. Huang, Eur. J. Org. Chem., 2754 (2014); doi:10.1002/ejoc.201301658