Main Article Content
Abstract
Polyethylene glycol (PEG) was found to be an effective and nontoxic reaction medium for the one-pot synthesis of functionalized pyrroles under catalyst-free conditions in excellent yields. Environmental acceptability, low cost, high yields and recyclability of the PEG are the important features of this protocol.
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Article Details
References
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References
D. O’Hagan, Nat. Prod. Rep., 17, 435 (2000); http://dx.doi.org/10.1039/a707613d.
C.T. Walsh, S. Garneau-Tsodikova and A.R. Howard-Jones, Nat. Prod. Rep., 23, 517 (2006); http://dx.doi.org/10.1039/b605245m.
J.W. Huffman, Curr. Med. Chem., 6, 705 (1999).
M. Kidwai, R. Venktaramanan, R. Mohan and P. Sapra, Curr. Med. Chem., 9, 1209 (2002); http://dx.doi.org/10.2174/0929867023370059.
G. La Regina, R. Silvestri, M. Artico, A. Lavecchia, E. Novellino, O. Befani, P. Turini and E. Agostinelli, Med. Chem., 50, 922 (2007); http://dx.doi.org/10.1021/jm060882y.
D.L. Boger, C.W. Boyce, M.A. Labroli, C.A. Sehon and Q. Jin, J. Am. Chem. Soc., 121, 54 (1999); http://dx.doi.org/10.1021/ja982078+.
M. Abid, S.M. Landge and B. Torok, Org. Prep. Proced. Int., 38, 495 (2006); http://dx.doi.org/10.1080/00304940609356444.
A. Facchetti, A. Abbotto, L. Beverina, M.E. van der Boom, P. Dutta, G. Evmenenko, G.A. Pagani and T.J. Marks, Chem. Mater., 15, 1064 (2003); http://dx.doi.org/10.1021/cm020929d.
S. Pu, G. Liu, L. Shen and J. Xu, Org. Lett., 9, 2139 (2007); http://dx.doi.org/10.1021/ol070622q.
O.V. Larionov and A. de Meijere, Angew. Chem. Int. Ed., 44, 5664 (2005); http://dx.doi.org/10.1002/anie.200502140.
G. Minetto, L.F. Raveglia, A. Sega and M. Taddei, Eur. J. Org. Chem., 5277 (2005); http://dx.doi.org/10.1002/ejoc.200500387.
C.M. Shiner and T.D. Lash, Tetrahedron, 61, 11628 (2005); http://dx.doi.org/10.1016/j.tet.2005.10.019.
S.J. Hwang, S.H. Cho and S. Chang, J. Am. Chem. Soc., 130, 16158 (2008); http://dx.doi.org/10.1021/ja806897h
M. Abid, L. Teixeira and B. Torok, Org. Lett., 10, 933 (2008); http://dx.doi.org/10.1021/ol703095d.
Y.D. La and B.A. Arndtsen, Angew. Chem. Int. Ed., 47, 5430 (2008); http://dx.doi.org/10.1002/anie.200801385.
W.A. Denny, G.W. Rewcastle and B.C. Baguley, J. Med. Chem., 33, 814 (1990); http://dx.doi.org/10.1021/jm00164a054.
E. Toja, D. Selva and P. Schiatti, J. Med. Chem., 27, 610 (1984); http://dx.doi.org/10.1021/jm00371a010.
V.J. Demopoulos and E. Rekka, J. Pharm. Sci., 84, 79 (1995); http://dx.doi.org/10.1002/jps.2600840119.
R.W. Burli, D. McMinn, J.A. Kaizerman, W. Hu, Y. Ge, Q. Pack, V. Jiang, M. Gross, M. Garcia, R. Tanaka and H.E. Moser, Bioorg. Med. Chem. Lett., 14, 1253 (2004); http://dx.doi.org/10.1016/j.bmcl.2003.12.042.
J. Lehuédé, B. Fauconneau, L. Barrier, M. Ourakow, A. Piriou and J.-M. Vierfond, Eur. J. Med. Chem., 34, 991 (1999); http://dx.doi.org/10.1016/S0223-5234(99)00111-7.
M. Del Poeta, W.A. Schell, C.C. Dykstra, S. Jones, R.R. Tidwell, A. Czarny, M. Bajic, M. Bajic, A. Kumar, D. Boykin and J.R. Perfect, Antimicrob. Agents Chemother., 42, 2495 (1998).
A. Hantzsch, Ber. Dtsch. Chem. Ges., 23, 1474 (1890); http://dx.doi.org/10.1002/cber.189002301243.
G. Kaupp, J. Schmeyers, A. Kuse and A. Atfeh, Angew. Chem. Int. Ed., 38, 2896 (1999); http://dx.doi.org/10.1002/(SICI)1521-3773(19991004)38:19<2896:: AID-ANIE2896>3.0.CO;2-3.
V.S. Matiychuk, R.L. Martyak, N.D. Obushak, Y.V. Ostapiuk and N.I. Pidlypnyi, Chem. Heterocycl. Compd., 40, 1218 (2004); http://dx.doi.org/10.1023/B:COHC.0000048299.17625.7f.
L. Knorr, Ber. Dtsch. Chem. Ges., 17, 1635 (1884); http://dx.doi.org/10.1002/cber.18840170220.
G.M. Manley, M.J. Kalman, B.G. Conway, C.C. Ball, J.L. Havens and R. Vaidyanathan, J. Org. Chem., 68, 6447 (2003); http://dx.doi.org/10.1021/jo034304q.
C.J. Nikhil, B.J. Prashant, V.P. Hemalata and N.T. Vikas, Tetrahedron Lett., 54, 3019 (2011).
S. Maiti, S. Biswas and U. Jana, J. Org. Chem., 75, 1674 (2010); http://dx.doi.org/10.1021/jo902661y.
L. Nagarapu, R. Mallepalli, L. Yeramanchi and R. Bantu, Tetrahedron Lett., 52, 3401 (2011); http://dx.doi.org/10.1016/j.tetlet.2011.04.095.
L. Nagarapu, R. Mallepalli, G. Arava and L. Yeramanchi, Eur. J. Chem., 1, 228 (2010); http://dx.doi.org/10.5155/eurjchem.1.3.228-231.172.
R. Mallepalli, L. Yeramanchi, R. Bantu and L. Nagarapu, Synlett, 2730 (2011); http://dx.doi.org/10.1055/s-0031-1289542.
L. Nagarapu, R. Mallepalli, U. Nikhil Kumar, P. Venkateswarlu, R. Bantu and L. Yeramanchi, Tetrahedron Lett., 53, 1699 (2012); http://dx.doi.org/10.1016/j.tetlet.2012.01.045.
M. Raghu, M. Rajasekhar, B. Chandra Obula Reddy, C. Suresh Reddy and B.V. Subba Reddy, Tetrahedron Lett., 54, 3503 (2013); http://dx.doi.org/10.1016/j.tetlet.2013.04.089.