Copyright (c) 2014 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Functionalization Reactions of Various Pyrazole-3-carboxylic Acid Chlorides with Some Ureas
Corresponding Author(s) : Ilhan Ozer Ilhan
Asian Journal of Chemistry,
Vol. 26 No. 8 (2014): Vol 26 Issue 8
Abstract
The 1H-pyrazole-3-carboxylic acids 2 or their remarkably stable acid chlorides 3 can easily be converted into the corresponding 1H-pyrazole-3-carbonyl-N'-urea derivatives (5a-k) from reaction with urea nucleophiles. It has been demonstrated that with the variation in reaction conditions, the reaction changes thus 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.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- E. Ziegler, M. Eder, C. Belegratis and E. Prewedourakis, Monatsh. Chem., 98, 2249 (1967); doi:10.1007/BF00902421.
- B. Altural, Y. Akçamur, E. Saripinar, İ. Yildirim and G. Kollenz, Monatsh. Chem., 120, 1015 (1989); doi:10.1007/BF00808773.
- İ. Yildirim, E. Saripinar, Y. Güzel, Ş. Patat and Y. Akçamur, J. Mol. Struct., 334, 165 (1995); doi:10.1016/0166-1280(94)04024-M.
- İ. Yildirim, M. Tezcan, Y. Güzel, E. Saripinar and Y. Akçamur, Turk J. Chem, 20, 27 (1996).
- İ. Yildirim and İ.Ö. İlhan, J. Heterocycl. Chem., 34, 1047 (1997); doi:10.1002/jhet.5570340353.
- E. Saripinar, I. Ozer Ilhan and Y. Akçamur, Heterocycles, 57, 1445 (2002); doi:10.3987/COM-02-9504.
- İ.Ö. İlhan, E. Saripinar and Y. Akçamur, J. Heterocycl. Chem., 42, 117 (2005); doi:10.1002/jhet.5570420117.
- Y. Akcamur, G. Penn, E. Ziegler, H. Sterk, G. Kollenz, K. Peters, E.-M. Peters and H.G. Schnering, Monatsh. Chem., 117, 231 (1986); doi:10.1007/BF00809443.
- Y. Akçamur, A. Şener, A.M. İpekoglu and G. Kollenz, J. Heterocycl. Chem., 34, 221 (1997); doi:10.1002/jhet.5570340133.
- A. Şener, M. Kasim Şener, I. Bildmci, R. Kasimogullari and Y. Akçamur, J. Heterocycl. Chem., 39, 869 (2002); doi:10.1002/jhet.5570390503.
- İ. Yildirim, F. Kandemirli and Y. Akçamur, J. Mol. Struct., 738, 275 (2005); doi:10.1016/j.molstruc.2004.12.026.
- İ. Yildirim, F. Kandemirli and E. Demir, Molecules, 10, 559 (2005); doi:10.3390/10030559.
- J.A. Joule, K. Mills and G.F. Smith, Heterocyclic Chemistry, Chapman & Hall: London, UK, edn, 3, Chap. 22, pp. 402-405 (1995).
- G. Daidone, D. Rafa, F. Plescia, B. Maggio and A. Roccaro, ARKIVOC, XI, 227 (2002).
- J. Elguero, in eds.: A.R. Katritzky and C.W. Rees, In: Comprehensive Heterocyclic Chemistry, Pergamon, Oxford, Vol. 5, p. 167 (1984).
- R.N. Mahajan, F.H. Havaldar and P.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, 17, 2165 (1998); doi:10.1080/07328319808004307.
- G.J. Hatheway, C. Hansch, K.H. Kim, S.R. Milstein, C.L. Schmidt, R.N. Smith and F.R. Quinn, J. Med. Chem., 21, 563 (1978); doi:10.1021/jm00204a012.
- R. Riedel, Drug Res., 31, 655 (1981).
- P.D. Mishra, S. Wahidullah and S.Y. Kamat, Indian J. Chem., 37B, 199 (1998).
- M. Londershausen, Pestic. Sci., 48, 269 (1996); doi:10.1002/(SICI)1096-9063(199612)48:4<269::AID-PS478>3.0.CO;2-B.
- M.R. Harnden, S. Bailey, M.R. Boyd, D.R. Taylor and N.D. Wright, J. Med. Chem., 21, 82 (1978); doi:10.1021/jm00199a015.
- A.G.A. Elagamey, F.A. El-Taweel, F.A. Amer and H.H. Zoorob, Arch. Pharm., 320, 246 (1987); doi:10.1002/ardp.19873200311.
- A.K. Tewari and A. Mishra, Bioorg. Med. Chem., 9, 715 (2001); doi:10.1016/S0968-0896(00)00285-6.
- P. Máatyus, J. Heterocycl. Chem., 35, 1075 (1998); doi:10.1002/jhet.5570350507.
- İ. Bildirici, A. Şener and I. Tozlu, Med. Chem. Res., 16, 418 (2007); doi:10.1007/s00044-007-9082-z.
- İ.Ö. İlhan, Y. Akçamur, E. Saripinar and E. Aslan, Asian J. Chem, 15, 1373 (2003).
- İ.Ö. İlhan, S. Zühal, Z. Önal and E. Saripinar, Heterocycl. Commun., 15, 279 (2009); doi:10.1515/HC.2009.15.4.279.
- İ.Ö. İlhan, Ö. Bahadir, Z. Önal and E. Saripinar, Asian J. Chem., 24, 141 (2012).
- İ.Ö. İlhan and M. Çadir, Asian J. Chem., 25, 1647 (2013); doi:10.14233/ajchem.2013.13625.
References
E. Ziegler, M. Eder, C. Belegratis and E. Prewedourakis, Monatsh. Chem., 98, 2249 (1967); doi:10.1007/BF00902421.
B. Altural, Y. Akçamur, E. Saripinar, İ. Yildirim and G. Kollenz, Monatsh. Chem., 120, 1015 (1989); doi:10.1007/BF00808773.
İ. Yildirim, E. Saripinar, Y. Güzel, Ş. Patat and Y. Akçamur, J. Mol. Struct., 334, 165 (1995); doi:10.1016/0166-1280(94)04024-M.
İ. Yildirim, M. Tezcan, Y. Güzel, E. Saripinar and Y. Akçamur, Turk J. Chem, 20, 27 (1996).
İ. Yildirim and İ.Ö. İlhan, J. Heterocycl. Chem., 34, 1047 (1997); doi:10.1002/jhet.5570340353.
E. Saripinar, I. Ozer Ilhan and Y. Akçamur, Heterocycles, 57, 1445 (2002); doi:10.3987/COM-02-9504.
İ.Ö. İlhan, E. Saripinar and Y. Akçamur, J. Heterocycl. Chem., 42, 117 (2005); doi:10.1002/jhet.5570420117.
Y. Akcamur, G. Penn, E. Ziegler, H. Sterk, G. Kollenz, K. Peters, E.-M. Peters and H.G. Schnering, Monatsh. Chem., 117, 231 (1986); doi:10.1007/BF00809443.
Y. Akçamur, A. Şener, A.M. İpekoglu and G. Kollenz, J. Heterocycl. Chem., 34, 221 (1997); doi:10.1002/jhet.5570340133.
A. Şener, M. Kasim Şener, I. Bildmci, R. Kasimogullari and Y. Akçamur, J. Heterocycl. Chem., 39, 869 (2002); doi:10.1002/jhet.5570390503.
İ. Yildirim, F. Kandemirli and Y. Akçamur, J. Mol. Struct., 738, 275 (2005); doi:10.1016/j.molstruc.2004.12.026.
İ. Yildirim, F. Kandemirli and E. Demir, Molecules, 10, 559 (2005); doi:10.3390/10030559.
J.A. Joule, K. Mills and G.F. Smith, Heterocyclic Chemistry, Chapman & Hall: London, UK, edn, 3, Chap. 22, pp. 402-405 (1995).
G. Daidone, D. Rafa, F. Plescia, B. Maggio and A. Roccaro, ARKIVOC, XI, 227 (2002).
J. Elguero, in eds.: A.R. Katritzky and C.W. Rees, In: Comprehensive Heterocyclic Chemistry, Pergamon, Oxford, Vol. 5, p. 167 (1984).
R.N. Mahajan, F.H. Havaldar and P.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, 17, 2165 (1998); doi:10.1080/07328319808004307.
G.J. Hatheway, C. Hansch, K.H. Kim, S.R. Milstein, C.L. Schmidt, R.N. Smith and F.R. Quinn, J. Med. Chem., 21, 563 (1978); doi:10.1021/jm00204a012.
R. Riedel, Drug Res., 31, 655 (1981).
P.D. Mishra, S. Wahidullah and S.Y. Kamat, Indian J. Chem., 37B, 199 (1998).
M. Londershausen, Pestic. Sci., 48, 269 (1996); doi:10.1002/(SICI)1096-9063(199612)48:4<269::AID-PS478>3.0.CO;2-B.
M.R. Harnden, S. Bailey, M.R. Boyd, D.R. Taylor and N.D. Wright, J. Med. Chem., 21, 82 (1978); doi:10.1021/jm00199a015.
A.G.A. Elagamey, F.A. El-Taweel, F.A. Amer and H.H. Zoorob, Arch. Pharm., 320, 246 (1987); doi:10.1002/ardp.19873200311.
A.K. Tewari and A. Mishra, Bioorg. Med. Chem., 9, 715 (2001); doi:10.1016/S0968-0896(00)00285-6.
P. Máatyus, J. Heterocycl. Chem., 35, 1075 (1998); doi:10.1002/jhet.5570350507.
İ. Bildirici, A. Şener and I. Tozlu, Med. Chem. Res., 16, 418 (2007); doi:10.1007/s00044-007-9082-z.
İ.Ö. İlhan, Y. Akçamur, E. Saripinar and E. Aslan, Asian J. Chem, 15, 1373 (2003).
İ.Ö. İlhan, S. Zühal, Z. Önal and E. Saripinar, Heterocycl. Commun., 15, 279 (2009); doi:10.1515/HC.2009.15.4.279.
İ.Ö. İlhan, Ö. Bahadir, Z. Önal and E. Saripinar, Asian J. Chem., 24, 141 (2012).
İ.Ö. İlhan and M. Çadir, Asian J. Chem., 25, 1647 (2013); doi:10.14233/ajchem.2013.13625.