Browse > Article
http://dx.doi.org/10.5012/bkcs.2014.35.4.994

Synthesis of Imidazo[1,2-a]pyridines and Pyrido[1,2-a]pyrimidines in Water and their SNAr Cyclizations  

Chanu, Langpoklakpam Gellina (Department of Chemistry, Manipur University)
Singh, Thokchom Prasanta (Department of Chemistry, Manipur University)
Jang, Yong Ju (Department of Chemistry and Research Institute of Life Science, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University)
Yoon, Yong-Jin (Department of Chemistry and Research Institute of Life Science, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University)
Singh, Okram Mukherjee (Department of Chemistry, Manipur University)
Lee, Sang-Gyeong (Department of Chemistry and Research Institute of Life Science, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University)
Publication Information
Bulletin of the Korean Chemical Society / v.35, no.4, 2014 , pp. 994-1000 More about this Journal
Abstract
Synthesis of tetrahydroimidazo[1,2-a]pyridines and tetrahydropyrido[1,2-a] pyrimidines by a one-pot and three component reaction of ${\alpha}$-oxoketenedithioacetals, diamines and DMAD in water has been described. Different routes for accessing the desired compounds were examined and a few specially designed-substrates have been utilized further to afford the new imidazo and pyrido fused [1,8] naphthyridine tetracyclic compound by $S_NAr$ intramolecular cyclization.
Keywords
Tetrahydroimidazo[1,2-a]pyridines; Tetrahy-dropyrido[1,2-a]pyrimidines; Imidazo and pyrido fused [1,8] naphthyridine tetracyclic; One-pot and multicomponent;
Citations & Related Records
연도 인용수 순위
  • Reference
1 (c) Alonso-Alija, C.; Michels, M.; Schirok, H.; Schlemmer, K. H.; Dodd, S.; Fitzgerald, M.; Bell, J.; Gill, A. Patent WO 2003053967, 2003.
2 Hranjec, M.; Kralj, M.; Piantanida, I.; Sedic, M.; Suman, L.; Pavelic, K.; Karminski-Zamola, G. J. Med. Chem. 2007, 50, 5696.   DOI   ScienceOn
3 Humphries, A. C.; Gancia, E.; Gilligan, M. T.; Goodacre, S.; Hallett, D.; Merchant, K. J.; Thomas, S. R. Bioorg. Med. Chem. Lett. 2006, 16, 1518.   DOI   ScienceOn
4 Smith, R. L.; Barette, R. J.; Sanders-Bush, E. J. Pharmacol. Exp. Ther. 1995, 275, 1050.
5 Awouters, F.; Vermeire, J.; Smeyers, F.; Vermote, P.; van Beek, R.; Niemegeers, C. J. E. Drug Dev. Res. 1986, 8, 95.   DOI
6 Yanagihara, Y.; Kasai, H.; Kawashima, T.; Shida, T. Jpn. J. Pharamacol. 1988, 48, 91.   DOI
7 Hajimahdi, Z.; Zarghi, A.; Zabihollahi, R.; Aghasadeghi, M. R. Med. Chem. Res. 2013, 22, 2467.   DOI
8 Huang, Z.-T.; Liu, Z.-R. Heterocycles 1986, 24, 2247.   DOI
9 (b) Wen, L. R.; Liu, C.; Li, M.; Wang, L. J. J. Org. Chem. 2010, 75, 7605.   DOI   ScienceOn
10 (c) Li, M.; Zhou, Z.-M.; Wen, L.-R.; Qiu, Z.-X. J. Org. Chem. 2011, 76, 3054.   DOI   ScienceOn
11 (d) Wen, L. R.; Li, Z. R.; Li, M.; Cao, H. Green Chem. 2012, 14, 707.   DOI   ScienceOn
12 (e) Wen, L. R.; Sun, Qi. C.; Zhang, H.-L.; Li, M. Org. Biomol. Chem. 2013, 11, 781.   DOI   ScienceOn
13 (f) Gupta, A. K.; Ila, H.; Junjappa, H. Synthesis 1988, 284.
14 (a) Singh, T. P.; Bhattarcharya, S.; Singh, O. M. Org. Lett. 2013, 15, 1974.   DOI   ScienceOn
15 (b) Devi, N. S.; Singh, S. J.; Devi, L. R.; Singh, O. M. Tetrahedron Lett. 2013, 54, 1432.   DOI   ScienceOn
16 (c) Devi, L. R.; Singh, O. M. Indian J. Chem: B 2012, 9, 1426.
17 (d) Devi, N. S.; Singh, S. J.; Singh, O. M. Synlett 2012, 23, 2111.   DOI   ScienceOn
18 (e) Singh, O. M.; Devi, L. R.; Singh, T. P.; Ila, H. Arkivoc 2011, ii, 297.
19 (f) Singh, O. M.; Devi, N. S.; Devi, L. R.; Lim, K. B.; Yoon, Y. J.; Lee, S. G. Bull. Korean Chem. Soc. 2011, 32, 175.   DOI   ScienceOn
20 (g) Singh, O. M.; Devi, N. S.; Thokchom, D. S.; Sharma, G. J. Eur. J. Med. Chem. 2010, 45, 2250.   DOI   ScienceOn
21 (i) Singh, O. M.; Devi, N. S. J. Org. Chem. 2009, 74, 3141.   DOI   ScienceOn
22 (a) Pan, L.; Bi, X.; Liu, Q. Chem. Soc. Rev. 2013, 42, 1251.   DOI   ScienceOn
23 (b) Junjappa, H.; Ila, H.; Asokan, C. V. Tetrahedron 1990, 46, 5423.   DOI   ScienceOn
24 (c) Ila, H.; Junjappa, H.; Mohanta, P. K. Progress in Heterocyclic Chemistry; Gribble, G. W., Gilchrist, T. L., Eds.; Pergamon: New York, 2001; p 1.
25 (c) Polshettiwar, V.; Varma, R. S. Chem. Soc. Rev. 2008, 37, 1546.   DOI   ScienceOn
26 Hesse, M. Alkaloid Chemistry; John Wiley & Sons: New York, 1981; p 47.
27 (a) Lindstrom, U. M. Chem. Rev. 2002, 102, 2751.   DOI   ScienceOn
28 (b) Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B. Angew. Chem. Int. Ed. 2005, 44, 3275.   DOI   ScienceOn
29 (a) Kazuo, K.; Noriki, I.; Isao, S.; Yasuo, I.; Hiroshige, H.; Masuo, M. US Patent 4186200, 1978.
30 (b) Frohn, M. J.; Hong, F. T.; Liu, L.; Lopez, P.; Siegmund, A. C.; Tadesse, S.; Tamayo, N. Patent WO 2005070932, 2005.
31 (h) Chanu, L. G.; Singh, O. M.; Jang, S. H.; Lee, S. G. Bull. Korean Chem. Soc. 2010, 31, 859.   DOI   ScienceOn
32 Revankar, G. R.; Matthews, J. R.; Robins, R. K. J. Med. Chem. 1975, 18, 1253.   DOI
33 Gudmundsson, K. S.; Williams, J. D.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 2003, 46, 1449.   DOI   ScienceOn
34 (a) Yan, S.; Chen, Y.; Liu, L.; He, N.; Lin, J. Green Chem. 2010, 12, 2043.   DOI   ScienceOn