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Copyright (c) 2014 Mayank Kinger*, V. D. Gupta, Joginder Singh, Avnish Kumar Arora, Vivek Sheel Jaswal
This work is licensed under a Creative Commons Attribution 4.0 International License.
Reaction of Heteroaryl Hydrazines with 3-Cinnamoyl-4-hydroxy-6-methyl-2H-pyran-2-ones: Synthesis of Some Novel Pyrazolines and their Iodine(III) Mediated Conversion to Corresponding Pyrazoles
Corresponding Author(s) : Mayank Kinger*
Asian Journal of Chemistry,
Vol. 26 No. 23 (2014)
Abstract
A series of some novel 5-aryl-3-(4-hydroxy-6-methyl-2H-pyran-2-oxo-3-yl)-1-heteroaryl pyrazolines have been prepared by the reaction of 3-cinnamoyl-4-hydroxy-6-methyl-2H-pyran-2-ones i.e., chalcone analogues of dehydroacetic acid (DHA) with various heteroaryl hydrazines and converted to corresponding pyrazoles with iodobenzene diacetate in good yields.
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- K.S. Girisha, B. Kalluraya, V. Narayana and Padmashree, Eur. J. Med. Chem., 45, 4640 (2010).
- B.S. Holla, M. Mahalinga, M.S. Karthikeyan, P.M. Akberali and N.S. Shetty, Bioorg. Med. Chem., 14, 2040 (2006).
- F. Manna, F. Chimenti, R. Fioravanti, A. Bolasco, D. Secci, P. Chimenti, C. Ferlini and G. Scambia, Bioorg. Med. Chem. Lett., 15, 4632 (2005).
- J.M. Fevig, J. Cacciola, J. Buriak Jr., K.A. Rossi, R.M. Knabb, J.M. Luettgen, P.C. Wong, S.A. Bai, R.R. Wexler and P.Y.S. Lam, Bioorg. Med. Chem. Lett., 16, 3755 (2006).
- M.G.C. Kahn, E. Konde, F. Dossou, D.C. Labaree, R.B. Hochberg and R.M. Hoyte, Bioorg. Med. Chem. Lett., 16, 3454 (2006).
- P. Cernuchová, G. Vo-Thanh, V. Milata, A. Loupy, S. Jantová and M. Theiszová, Tetrahedron, 61, 5379 (2005).
- Z. Sui, J. Guan, M.P. Ferro, K. McCoy, M.P. Wachter, W.V. Murray, M. Singer, M. Steber, D.M. Ritchie and D.C. Argentieri, Bioorg. Med. Chem. Lett., 10, 601 (2000).
- G.A. Golubeva, Ph. D. Thesis, Moscow University (1962).
- I. Bhatnagar and M.V. George, Tetrahedron, 24, 1293 (1968).
- O. Prakash, M. Kumar, R. Kumar, C. Sharma and K.R. Aneja, Eur. J. Med. Chem., 45, 4252 (2010).
- O. Prakash, A. Kumar, M. Kinger and S.P. Singh, Indian J. Chem., 44B, 456 (2006).
- R. Aggarwal, V. Kumar and S.P. Singh, Indian J. Chem., 46B, 1332 (2007).
- R. Filler, V.D. Beaucaire and H.H. Kang, J. Org. Chem., 40, 935 (1975).
- R.H. Wiley, C.H. Jarboe and H.G. Ellert, J. Am. Chem. Soc., 77, 5102 (1955).
References
K.S. Girisha, B. Kalluraya, V. Narayana and Padmashree, Eur. J. Med. Chem., 45, 4640 (2010).
B.S. Holla, M. Mahalinga, M.S. Karthikeyan, P.M. Akberali and N.S. Shetty, Bioorg. Med. Chem., 14, 2040 (2006).
F. Manna, F. Chimenti, R. Fioravanti, A. Bolasco, D. Secci, P. Chimenti, C. Ferlini and G. Scambia, Bioorg. Med. Chem. Lett., 15, 4632 (2005).
J.M. Fevig, J. Cacciola, J. Buriak Jr., K.A. Rossi, R.M. Knabb, J.M. Luettgen, P.C. Wong, S.A. Bai, R.R. Wexler and P.Y.S. Lam, Bioorg. Med. Chem. Lett., 16, 3755 (2006).
M.G.C. Kahn, E. Konde, F. Dossou, D.C. Labaree, R.B. Hochberg and R.M. Hoyte, Bioorg. Med. Chem. Lett., 16, 3454 (2006).
P. Cernuchová, G. Vo-Thanh, V. Milata, A. Loupy, S. Jantová and M. Theiszová, Tetrahedron, 61, 5379 (2005).
Z. Sui, J. Guan, M.P. Ferro, K. McCoy, M.P. Wachter, W.V. Murray, M. Singer, M. Steber, D.M. Ritchie and D.C. Argentieri, Bioorg. Med. Chem. Lett., 10, 601 (2000).
G.A. Golubeva, Ph. D. Thesis, Moscow University (1962).
I. Bhatnagar and M.V. George, Tetrahedron, 24, 1293 (1968).
O. Prakash, M. Kumar, R. Kumar, C. Sharma and K.R. Aneja, Eur. J. Med. Chem., 45, 4252 (2010).
O. Prakash, A. Kumar, M. Kinger and S.P. Singh, Indian J. Chem., 44B, 456 (2006).
R. Aggarwal, V. Kumar and S.P. Singh, Indian J. Chem., 46B, 1332 (2007).
R. Filler, V.D. Beaucaire and H.H. Kang, J. Org. Chem., 40, 935 (1975).
R.H. Wiley, C.H. Jarboe and H.G. Ellert, J. Am. Chem. Soc., 77, 5102 (1955).