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Synthesis and Characterization of Imidazo[1,2-a]pyridines and Zolimidine
Corresponding Author(s) : Narva Deshwar Kushwaha
Asian Journal of Chemistry,
Vol. 29 No. 7 (2017): Vol 29 Issue 7
Abstract
A convenient and efficient synthesis, without any organic solvent or catalyst is described for the preparation of imidazo[1,2-a]pyridine derivatives. The reaction has been done between 2-aminopyridines and a-bromoacetone derivatives in good to excellent yields in water. In several cases the isolation does not require any chromatography for purification. The reaction thus developed has been applied for quick synthesis of zolimidine with 91 % yield.
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References
N. Shapiro and A. Vigalok, Angew. Chem., 120, 2891 (2008); https://doi.org/10.1002/ange.200705347.
(a) H.C. Hailes, Org. Process Res. Dev., 11, 114 (2007); https://doi.org/10.1021/op060157x. (b) C.J. Li and T.H. Chan, in eds.: P.A. Grieco, Organic Synthesis in Water, Thomson Science: Glasgow: Scotland (1998). (c) C.J. Li and T.H. Chan, Organic Reactions in Aqueous Media, Wiley:New York (1997). (d) C.J. Li, Chem. Rev., 105, 3095 (2005); https://doi.org/10.1021/cr030009u.
M. Adib, M. Mahdavi, M.A. Noghani and P. Mirzaei, Tetrahedron Lett.,48, 7263 (2007); https://doi.org/10.1016/j.tetlet.2007.08.049.
A.S. Howard, in eds.: A.R. Katritzky, C.W. Rees and E.V.F. Scriven, In Comprehensive Heterocyclic Chemistry, Pergamon Press: London, vol. 8, Chap. 10, pp 262, and references therein (1996).
F. Couty and G. Evano, in eds.: A.R. Katritzky, C.A. Ramsden, E.V.F. Scriven and J.K.R. Taylor, In Comprehensive Heterocyclic Chemistry III, Elsevier Science, Oxford, vol. 11, Chap. 10, pp. 409, and references therein (2008).
(a) A.R. Katritzky, Y.J. Xu and H. Tu, J. Org. Chem., 68, 4935 (2003); https://doi.org/10.1021/jo026797p. (b) S.Z. Langer, S. Arbilla, J. Benavides and B. Scatton, Adv. Biochem. Psychopharmacol., 46, 61 (1990). (c) G.M. Carminati, Farmaco Ed., 33, 68 (1978). (d) J. Allen, G. Parent and A. Tizot, J. Labelled Comp. Radiopharm., 23, 807 (1986); https://doi.org/10.1002/jlcr.2580230803.
(a) M. Adib, E. Sheikhi and N. Rezaei, Tetrahedron Lett., 52, 3191 (2011); https://doi.org/10.1016/j.tetlet.2011.04.002. (b) A.B. Ramesha, G.M. Raghavendra, K.N. Nandeesh, K.S. Rangappa and K. Mantelingu, Tetrahedron Lett., 54, 95 (2013); https://doi.org/10.1016/j.tetlet.2012.10.112.
(a) A.T. Khan, R. Sidick Basha and M. Lal, Tetrahedron Lett., 53, 2211 (2012); https://doi.org/10.1016/j.tetlet.2012.02.078. (b) K. Groebke, L. Weber and F. Mehlin, Synlett, 661 (1998); https://doi.org/10.1055/s-1998-1721. (c) C. Blackburn, Tetrahedron Lett., 39, 5469 (1998); https://doi.org/10.1016/S0040-4039(98)01113-7. (d) H. Bienayme and K. Bouzid, Angew. Chem. Int. Ed., 37, 2234 (1998); https://doi.org/10.1002/(SICI)1521-3773(19980904)37:16<2234::AIDANIE2234>3.0.CO;2-R.
(a) A. Gueiffier, S. Mavel, M. Lhassani, A. Elhakmaoui, R. Snoeck, G. Andrei, O. Chavignon, J.-C. Teulade, M. Witvrouw, J. Balzarini, E. De Clercq and J.-P. Chapat, J. Med. Chem., 41, 5108 (1998); https://doi.org/10.1021/jm981051y. (b) J.E. Starrett, T.A. Montzka, A.R. Crosswell and R.L. Cavanagh, J. Med. Chem., 32, 2204 (1989); https://doi.org/10.1021/jm00129a028. (c) A. Chaouni-Benabdallah, C. Galtier, H. Allouchi, A. Kherbeche, O. Chavignon, J.-C. Teulade, M. Witvrouw, C. Pannecouque, R. Snoeck, G. Andrei, J. Balzarini, E. De Clercq, F. Fauvelle, C. Enguehard and A. Gueiffier, Chem. Pharm. Bull. (Tokyo), 49, 1631 (2001); https://doi.org/10.1248/cpb.49.1631.
S. Mavel, J.-L. Renou, C. Galtier, H. Allouchi, R. Snoeck and G. Andrei, Bioorg. Med. Chem., 10, 941 (2002); https://doi.org/10.1016/S0968-0896(01)00347-9.
R.S. Varma and D. Kumar, Tetrahedron Lett., 40, 7665 (1999); https://doi.org/10.1016/S0040-4039(99)01585-3.
S.M. Ireland, H. Tye and M. Whittaker, Tetrahedron Lett., 44, 4369 (2003); https://doi.org/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); https://doi.org/10.1016/j.tetlet.2005.11.152.
A. Shaabani, E. Soleimani and A. Maleki, Tetrahedron Lett., 47, 3031 (2006); https://doi.org/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); https://doi.org/10.1016/j.bmcl.2009.06.045. (b) M.C. Pirrung, S. Ghorai and T.R. Ibarra-Rivera, J. Org. Chem., 74, 4110 (2009); https://doi.org/10.1021/jo900414n. (c) S.K. Guchhait and C. Madaan, Synlett, 628 (2009); https://doi.org/10.1055/s-0028-1087915. (d) M. Nayak, S. Kanojiya and S. Batra, Synthesis, 431 (2009); https://doi.org/10.1055/s-0028-1083306. (e) A. Shaabani, E. Soleimani, A. Maleki and J. Moghimi-Rad, Synth. Commun., 38, 1090 (2008); https://doi.org/10.1080/00397910701862931. (f) F. Mert-Balci, J. Conrad, U. Beifuss, K. Meindl, T. Schulz, D. Stalke and U. Beifuss, Synthesis, 3649 (2008); https://doi.org/10.1055/s-0028-1083602. (g) A.L. Rousseau, P. Matlaba and C.J. Parkinson, Tetrahedron Lett., 48, 4079 (2007); https://doi.org/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); https://doi.org/10.1248/cpb.55.957. (i) V.G. Nenajdenko, A.L. Reznichenko and E.S. Balenkova, Russ. Chem. Bull., 56, 560 (2007); https://doi.org/10.1007/s11172-007-0093-1.
C. He, J. Hao, H. Xu, Y. Mo, H. Liu, J. Han and A. Lei, Chem. Commun., 48, 11073 (2012); https://doi.org/10.1039/c2cc35927h.
Q. Cai, M.-C. Liu, B.-M. Mao, X. Xie, F.-C. Jia, Y.-P. Zhu and A.-X. Wu, Chin. Chem. Lett., 26, 881 (2015); https://doi.org/10.1016/j.cclet.2014.12.016.
D.N. Kommi, P.S. Jadhavar, D. Kumar and A.K. Chakraborti, Green Chem., 15, 798 (2013); https://doi.org/10.1039/c3gc37004f.