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Synthesis of N-Arylisatins Using Different Heterogeneous Catalyst Under Microwave Irradiations
Corresponding Author(s) : Ravinder Singh
Asian Journal of Chemistry,
Vol. 25 No. 9 (2013): Vol 25 Issue 9
Abstract
N-Arylisatins having both biological and medical properties are synthesized by the reaction of methyl-2-oxo-2-(arylamino)acetates and arynes using NaHCO3 in presence of different heterogeneous catalyst under microwave irradiations in high yield in shorter reaction time.
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- (a) S.N. Pandeya, S. Samitha, M. Jyoti and S.K. Sridhar, Acta Pharm., 55, 27 (2005); (b) K.L. Vine, L. Matesh, J.M. Locke, M. Ranson, D. Kropeta, Med Chem., 9, 397 (2009); (c) S.J. Shultleworth, D. Nasturica, C. Gervais, M.A. Siddiqui, R.F. Rando and N. Lee, Bioorg. Med. Chem. Lett., 10, 250 (2000).
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- K.J. Kilpin, W. Henderson and B.K. Nicholson, Polyhedron, 26, 2004 (2007).
- M.R. Islam, J. Abedin and K. Khayer, Indian J. Chem., 40B, 240 (2001).
- R.S. Varma and I.A. Khan, Polish J. Pharmacol. Pharm., 29, 549 (1977).
- C. Li, Y. Go, Z. Mao, K. Koyano, Y. Kai, N. Kanesha, Q. Zhu, Z. Zho and S. Wu, Bull. Chem. Soc. (Japan), 69, 1621 (1996).
- T.A. Mcnell, Antimicrob. Agents Chemother., 4, 105 (1973).
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- (a) Y. Chem and R.C. Larock, in ed.: J. Ackerman, In Modern Arylation Methods, Wiley/VCH New York (2009); (b) R. Sanz, Org. Prep. Proced. Int., 40, 215 (2008).
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- Z. Liu and R.C. Larock, J. Am. Chem. Soc., 127, 13112 (2005).
- D.G. Pintori and M.F. Greaney, Org. Lett., 12, 168 (2010).
- H. Yoshida, E. Shirakawa, Y. Honda and T. Hiyama, Angew. Chem. Int. Ed., 41, 3246 (2002).
- J. Zhao and R.C. Larock, J. Org. Chem., 72, 583 (2007).
- D.C. Rogness and R.C. Larock, Tetrahedron Lett., 50, 4003 (2009).
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- S. Peddibhotla, Curr. Bioact. Compd., 5, 20 (2009).
References
(a) S.N. Pandeya, S. Samitha, M. Jyoti and S.K. Sridhar, Acta Pharm., 55, 27 (2005); (b) K.L. Vine, L. Matesh, J.M. Locke, M. Ranson, D. Kropeta, Med Chem., 9, 397 (2009); (c) S.J. Shultleworth, D. Nasturica, C. Gervais, M.A. Siddiqui, R.F. Rando and N. Lee, Bioorg. Med. Chem. Lett., 10, 250 (2000).
M.R. Islam, M.J. Abedin, M.M. Hossain and H.J. Doddeck, Bangladesh Chem. Soc., 11, 71 (1998).
K.J. Kilpin, W. Henderson and B.K. Nicholson, Polyhedron, 26, 2004 (2007).
M.R. Islam, J. Abedin and K. Khayer, Indian J. Chem., 40B, 240 (2001).
R.S. Varma and I.A. Khan, Polish J. Pharmacol. Pharm., 29, 549 (1977).
C. Li, Y. Go, Z. Mao, K. Koyano, Y. Kai, N. Kanesha, Q. Zhu, Z. Zho and S. Wu, Bull. Chem. Soc. (Japan), 69, 1621 (1996).
T.A. Mcnell, Antimicrob. Agents Chemother., 4, 105 (1973).
(a) R. Romagnoli, P.G. Baraldi, C. Cruz-Lopez, D. Preti, J. Bermejo and F. Estavez, Chem. Med. Chem., 4, 1668 (2009); (b) M.G. Bursavich, A.M. Gilbert, S. Lombardi, K.E. Georgiadis, E. Reifenberg, C.R. Flannery and E.A. Morris,Bioorg. Med. Chem. Lett., 17, 5630 (2007); (c) M.J. Konkel, M. Packiarajan, H. Chem, U.P. Topiwala, H. Jimenez, I.J. Talisman, H. Coate and M.W. Walker, Bioorg. Med. Chem. Lett., 16, 3950 (2006); (d) P.Y.S. Lam, G. Vinoent, C.G. Clark, S. Dcudon and P.K. Jadhav, Tetrahedron Lett., 42, 3415 (2001).
(a) A.V. Shindikar, F. Khan and C.L. Viswanathan, Eur. J. Med. Chem., 41, 786 (2006); (b) P. Moser, A. Sallmann and I.J. Wieserberg, Med. Chem., 33, 2358 (1990); (c) R. Sarges, H.R. Howard, H.K. Koe and A. Weissman, J. Med. Chem., 32, 437 (1989).
N. Peet, J. Heterocycl. Chem., 17, 1514 (1990).
(a) Y. Chem and R.C. Larock, in ed.: J. Ackerman, In Modern Arylation Methods, Wiley/VCH New York (2009); (b) R. Sanz, Org. Prep. Proced. Int., 40, 215 (2008).
(a) Z. Lin and R.C. Larock, J. Org. Chem., 71, 3198 (2006); (b) Z. Lin and R.C. Larock, Org. Lett., 5, 4673 (2003); (c) Z. Lin and R.C. Larock, Org. Lett., 6, 99 (2004).
Z. Liu and R.C. Larock, J. Am. Chem. Soc., 127, 13112 (2005).
D.G. Pintori and M.F. Greaney, Org. Lett., 12, 168 (2010).
H. Yoshida, E. Shirakawa, Y. Honda and T. Hiyama, Angew. Chem. Int. Ed., 41, 3246 (2002).
J. Zhao and R.C. Larock, J. Org. Chem., 72, 583 (2007).
D.C. Rogness and R.C. Larock, Tetrahedron Lett., 50, 4003 (2009).
Z. Lin and R.C. Larock, J. Org. Chem., 71, 3198 (2006).
S. Peddibhotla, Curr. Bioact. Compd., 5, 20 (2009).