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Reactions of Some Pyrazole-3-Carboxylic Acid Chlorides with Various Anilides
Corresponding Author(s) : Ilhan Özer Ilhan
Asian Journal of Chemistry,
Vol. 25 No. 3 (2013): Vol 25 Issue 3
Abstract
1H-pyrazole-3-carboxylic acid chlorides (3) can easily be converted into the corresponding 1H-pyrazole-3-carboxamide (5) by reaction with various anilides. It has been demonstrated that with the variation in reaction conditions, the reaction changes leading to different products. All newly synthesized compounds were characterized by elemental analysis, FT-IR, 1H and 13C NMR spectral data. All compounds were compared with their previous analogues.
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- E. Ziegler, M. Eder, C. Belegratis and E. Prewedourakis, Monatsh. Chem., 98, 2249 (1967).
- R.W. Saalfrank, T. Lutz, B. Hörner, J. Gündel, K. Peters and H.G. von Schnering, Chem. Ber., 124, 2289 (1991).
- T. Hökelek, E. Saripinar, I. Yildirim, M. Akkurt and Y. Akçamur, Acta Crystallogr. E., 58, 30 (2002).
- E. Ziegler, G. Kollenz, M. Eder and H. Igel, Monatsh. Chem., 102, 1769 (1971).
- W. Ott, E. Ziegler and G. Kollenz, Synthesis, 477 (1976).
- G. Kollenz, G. Penn, G. Dolenz, Y. Akçamur, K. Peters, E.M. Peters and H.G. von Schnering, Chem. Ber., 117, 1299 (1984).
- G. Kollenz, C.O. Kappe and H.A.A. El-Nabi, Heterocycles, 32, 669 (1991).
- I. Yildirim and I. Ö. Ilhan, J. Heterocycl. Chem., 34, 1047 (1997).
- B. Altural, Y. Akçamur, E. Saripinar, I. Yildirim and G. Kollenz, Monatsh. Chem., 120, 1015 (1989).
- I. Yildirim, E. Saripinar, Y. Güzel, S. Patat and Y.Akçamur, J. Mol. Struct. (Theochem.), 334, 165 (1995).
- I. Yildirim, M. Tezcan, Y. Güzel, E. Saripinar and Y. Akçamur, Turkish J. Chem., 20, 27 (1996).
- E. Saripinar, I. Yildirim, Y. Güzel and Y. Akçamur, Monatsh. Chem., 127, 505 (1996).
- I. Yildirim and F. Kandemirli, Heteroatom Chem., 15, 9 (2004).
- Y. Akçamur, G. Penn, E. Ziegler, H. Sterk, G. Kollenz, K. Peters, E.M. Peters and H.G. von Schnering, Monatsh. Chem., 117, 231 (1986).
- Y. Akçamur, A. Sener, A.M. Ipekoglu and G.Kollenz, J. Heterocycl. Chem., 34, 221 (1997).
- A. Sener, R. Kasimogullari, M.K. Sener, I. Bildirici and Y. Akçamur, J. Heterocycl. Chem., 39, 869 (2002).
- J.A. Joule, K. Mills and G.F. Smith, Heterocyclic Chemistry (edn. 3), Chapman and Hall, London, UK 402-405 (Chapter 22) (1995).
- R.H. Wiley, in ed.:A. Weissberger, Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings, The Chemistry of Heterocyclic Compounds, Interscience Publishers, New York, vol. 22, pp. 180-278 (1967).
- J. Elguero, A.R. Katritzky and C.W. Rees, Editors, In Comprehensive Heterocyclic Chemistry, Oxford, Pergamon, vol. 5, pp. 167-302 (1984).
- G. Daidone, D. Raffa, F. Plescia, B. Maggio and A. Roccaro, Arkivoc, 227 (2002).
- J. Elguero, P. Goya, N. Jagerovic and A.M.S. Silva, in eds.: O.A. Attanasi and D. Spinelli, Pyrazoles as Drugs: Facts and Fantasies. In Targets in Heterocyclic Systems; Royal Society of Chemistry: Cambridge, vol. 6, pp. 52-98 (2002).
- R.N. Mahajan, F.H. Havaldar and S. Fernandes, J. Indian Chem. Soc., 68, 245 (1991).
- P.G. Baraldi, S. Manfredini, R. Romagnoli, L. Stevanato, A.N. Zaid and R. Manservigi, Nucleosides Nucleotides and Nucleic Acids, 17, 2165 (1998).
- G.J. Hatheway, C. Hansch, K.H. Kim, S.R. Milstein, C.L. Schimidt, R.N. Smith and F.R. Quin, J. Med. Chem., 21, 563 (1978).
- R. Riedel, Arzneimittel-Forschung-Drug Res., 31, 655 (1981).
- P.D. Mishra, S. Wahidullah and S.Y. Kamat,Indian J. Chem., 37B, 199 (1998).
- M. Londershausen, J. Pestic. Sci., 48, 269 (1996).
- M.R. Harnden, S. Bailey, M.R. Boyd, D.R. Taylor and N.D. Wright, J. Med. Chem., 21, 82 (1978).
- A.G.A. Elagamey, F.A. El-Taweel, F.A. Amer and H.H. Zoorob, Arch. Pharm., 320, 246 (1987).
- I. Bildirici, A. Sener and I. Tozlu, Med. Chem. Res., 16, 418 (2007).
- I.Ö. Ilhan, Y. Akçamur, E. Saripinar and E. Aslan, Asian J. Chem., 15, 1373 (2003).
- I.Ö. Ilhan, S. Zühal, Z. Önal and E. Saripinar, Heterocycl. Commun.,15, 279 (2009).
- I.Ö. Ilhan, Ö. Bahadir, Z. Önal and E. Saripinar, Asian J. Chem., 24,141 (2012).
References
E. Ziegler, M. Eder, C. Belegratis and E. Prewedourakis, Monatsh. Chem., 98, 2249 (1967).
R.W. Saalfrank, T. Lutz, B. Hörner, J. Gündel, K. Peters and H.G. von Schnering, Chem. Ber., 124, 2289 (1991).
T. Hökelek, E. Saripinar, I. Yildirim, M. Akkurt and Y. Akçamur, Acta Crystallogr. E., 58, 30 (2002).
E. Ziegler, G. Kollenz, M. Eder and H. Igel, Monatsh. Chem., 102, 1769 (1971).
W. Ott, E. Ziegler and G. Kollenz, Synthesis, 477 (1976).
G. Kollenz, G. Penn, G. Dolenz, Y. Akçamur, K. Peters, E.M. Peters and H.G. von Schnering, Chem. Ber., 117, 1299 (1984).
G. Kollenz, C.O. Kappe and H.A.A. El-Nabi, Heterocycles, 32, 669 (1991).
I. Yildirim and I. Ö. Ilhan, J. Heterocycl. Chem., 34, 1047 (1997).
B. Altural, Y. Akçamur, E. Saripinar, I. Yildirim and G. Kollenz, Monatsh. Chem., 120, 1015 (1989).
I. Yildirim, E. Saripinar, Y. Güzel, S. Patat and Y.Akçamur, J. Mol. Struct. (Theochem.), 334, 165 (1995).
I. Yildirim, M. Tezcan, Y. Güzel, E. Saripinar and Y. Akçamur, Turkish J. Chem., 20, 27 (1996).
E. Saripinar, I. Yildirim, Y. Güzel and Y. Akçamur, Monatsh. Chem., 127, 505 (1996).
I. Yildirim and F. Kandemirli, Heteroatom Chem., 15, 9 (2004).
Y. Akçamur, G. Penn, E. Ziegler, H. Sterk, G. Kollenz, K. Peters, E.M. Peters and H.G. von Schnering, Monatsh. Chem., 117, 231 (1986).
Y. Akçamur, A. Sener, A.M. Ipekoglu and G.Kollenz, J. Heterocycl. Chem., 34, 221 (1997).
A. Sener, R. Kasimogullari, M.K. Sener, I. Bildirici and Y. Akçamur, J. Heterocycl. Chem., 39, 869 (2002).
J.A. Joule, K. Mills and G.F. Smith, Heterocyclic Chemistry (edn. 3), Chapman and Hall, London, UK 402-405 (Chapter 22) (1995).
R.H. Wiley, in ed.:A. Weissberger, Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings, The Chemistry of Heterocyclic Compounds, Interscience Publishers, New York, vol. 22, pp. 180-278 (1967).
J. Elguero, A.R. Katritzky and C.W. Rees, Editors, In Comprehensive Heterocyclic Chemistry, Oxford, Pergamon, vol. 5, pp. 167-302 (1984).
G. Daidone, D. Raffa, F. Plescia, B. Maggio and A. Roccaro, Arkivoc, 227 (2002).
J. Elguero, P. Goya, N. Jagerovic and A.M.S. Silva, in eds.: O.A. Attanasi and D. Spinelli, Pyrazoles as Drugs: Facts and Fantasies. In Targets in Heterocyclic Systems; Royal Society of Chemistry: Cambridge, vol. 6, pp. 52-98 (2002).
R.N. Mahajan, F.H. Havaldar and S. Fernandes, J. Indian Chem. Soc., 68, 245 (1991).
P.G. Baraldi, S. Manfredini, R. Romagnoli, L. Stevanato, A.N. Zaid and R. Manservigi, Nucleosides Nucleotides and Nucleic Acids, 17, 2165 (1998).
G.J. Hatheway, C. Hansch, K.H. Kim, S.R. Milstein, C.L. Schimidt, R.N. Smith and F.R. Quin, J. Med. Chem., 21, 563 (1978).
R. Riedel, Arzneimittel-Forschung-Drug Res., 31, 655 (1981).
P.D. Mishra, S. Wahidullah and S.Y. Kamat,Indian J. Chem., 37B, 199 (1998).
M. Londershausen, J. Pestic. Sci., 48, 269 (1996).
M.R. Harnden, S. Bailey, M.R. Boyd, D.R. Taylor and N.D. Wright, J. Med. Chem., 21, 82 (1978).
A.G.A. Elagamey, F.A. El-Taweel, F.A. Amer and H.H. Zoorob, Arch. Pharm., 320, 246 (1987).
I. Bildirici, A. Sener and I. Tozlu, Med. Chem. Res., 16, 418 (2007).
I.Ö. Ilhan, Y. Akçamur, E. Saripinar and E. Aslan, Asian J. Chem., 15, 1373 (2003).
I.Ö. Ilhan, S. Zühal, Z. Önal and E. Saripinar, Heterocycl. Commun.,15, 279 (2009).
I.Ö. Ilhan, Ö. Bahadir, Z. Önal and E. Saripinar, Asian J. Chem., 24,141 (2012).