Synthesis and studies of pyrazolo[3,4-b]piperidin-4-one derivatives

Hussain Ali Soleiman; Ali Kamel Khalafallah; Hana'a Abd-Ellatif

doi:10.5155/eurjchem.3.3.287-292.611

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Published: Sep 30, 2012

DOI: https://doi.org/10.5155/eurjchem.3.3.287-292.611

Keywords:

Pyrazole, Isoxazolo, Pyrimidine, Spiro β-lactam, Pyrimidine thione, Spiro thiazolodine

Section

Research Article

Issue

Vol. 3 No. 3 (2012): September 2012

Dates

Received 2012-04-10
Accepted 2012-07-08
Published 2012-09-30

Hussain Ali Soleiman

Chemistry Department, Aswan Faculty of Science, South Valley University, Aswan, 81111, Egypt

Ali Kamel Khalafallah

Chemistry Department, Aswan Faculty of Science, South Valley University, Aswan, 81111, Egypt

Hana'a Abd-Ellatif

Chemistry Department, Aswan Faculty of Science, South Valley University, Aswan, 81111, Egypt

Abstract

A series of isolated/fused of pyrazole, isoxazolo, pyrimidine, pyrimidine thione, spiro thiazolodine and spiro β-lactam derivatives incorporating to 4-acetyl-5-amino-3-methyl-1-phenyl-2-pyrazoline have been synthesized by different methods of chemical reactions. The structure assignments of these compounds, based on chemical and spectroscopic evidence were deduced from their IR, ¹H NMR, elemental analysis and mass spectrometry.

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Soleiman, H. A.; Khalafallah, A. K.; Abd-Ellatif, H. Synthesis and Studies of pyrazolo[3,4-b]piperidin-4-One Derivatives. Eur. J. Chem. 2012, 3, 287-292.

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References

[1]. Heaney, H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: New York, 1991; Vol. 2, pp. 953-973.
http://dx.doi.org/10.1016/B978-0-08-052349-1.00053-6

[2]. Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044-1070.
http://dx.doi.org/10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO;2-E

[3]. Denmark, S. E.; Nicaise, O. J. C. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Springer, Heidelberg, 1999, Vol. 2, pp. 923-964.

[4]. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069-1094.
http://dx.doi.org/10.1021/cr980414z
PMid:11749440

[5]. Cordova, A. Acc. Chem. Res. 2004, 93, 522-528.

[6]. Newkome, G. R.; Moorefield, C. N.; Vogtle, F. Dendrimers and Dendrons; Wiley-VCH: Verlag GmbH, 2002.

[7]. Dendrimers and Other Dendritic Polymers; Frechet, J. M. J.; Tomalia, D. A., Eds.; John Wiley & Sons: Chichester, 2001.

[8]. Dendrimers in Catalysis; Topics in Organometallic Chemistry; Gade, L. H., Eds.; Springer-Verlag: Heidelberg, 2006; Vol. 20, 1-42.

[9]. Mery, D.; Astruc, D. Coord. Chem. Rev. 2006, 250(15-16), 1965-1979.
http://dx.doi.org/10.1016/j.ccr.2005.11.012

[10]. Helms, B.; Frechet, J. M. J. Adv. Synth. Catal. 2006, 348, 1125-1148
http://dx.doi.org/10.1002/adsc.200606095

[11]. Astruc, D.; Heuze, K.; Gatard, S.; Mery, D.; Nlate, S.; Plault, L. Adv. Synth. Catal. 2005, 347, 329-338.
http://dx.doi.org/10.1002/adsc.200404247

[12]. Astruc, D.; Chardac, F. Chem. Rev. 2001, 101, 2991-3023.
http://dx.doi.org/10.1021/cr010323t
PMid:11749398

[13]. Ooosterom, G. E.; Reek, J. N. H.; Kamer, P. C. J.; VanLeeuwen, P. W. N. M. Angew. Chem. Int. Ed. 2001, 40, 1828-1849.
http://dx.doi.org/10.1002/1521-3773(20010518)40:10<1828::AID-ANIE1828>3.0.CO;2-Y

[14]. Scot, R. W. J.; Wilson, O. M.; Crooks, R. M. J. Phys. Chem. B. 2005, 109, 692-704.
http://dx.doi.org/10.1021/jp0469665
PMid:16866429

[15]. Wu, H.; Chen, X.; Wan, Y.; Ye, L.; Xin, H.; Xu, H.; Yue, C.; Pang, L.; Ma, R. Shi, D. Tetrahedron Lett. 2009, 50, 1062-1065.
http://dx.doi.org/10.1016/j.tetlet.2008.12.067

[16]. Dziedzic, V.; Ibrahem, I.; Cordova, A. Tetrahedron Lett. 2008, 49, 803-807.
http://dx.doi.org/10.1016/j.tetlet.2007.11.196

[17]. Hayashi, Y.; Urushima, T.; Aratake, S.; Okano, T.; Obi, K. Org. Lett. 2008, 10(1), 21-24.
http://dx.doi.org/10.1021/ol702489k
PMid:18052181

[18]. Khan, A. T.; Pravin, T.; Choudhary, L. H. Eur. J. Org. Chem. 2008, 834-839.
http://dx.doi.org/10.1002/ejoc.200700643

[19]. Bigdeli, M. A.; Nemati, F.; Mahdavinia, G. H. Tetrahedron Lett. 2007, 48, 6801-6804.
http://dx.doi.org/10.1016/j.tetlet.2007.07.088

[20]. Guo, Q. X.; Liu, H.; Guo, C.; Luo, S. W.; Gu, Y.; Gong, L. Z. J. Am. Chem. Soc. 2007, 129, 3790-3791.
http://dx.doi.org/10.1021/ja068236b
PMid:17358062

[21]. Wang, R.; Li, B. G.; Huang, T. K.; Shi, L.; Lu, X. X. Tetrahedron Lett. 2007, 48, 2071-2073.
http://dx.doi.org/10.1016/j.tetlet.2007.01.142

[22]. Wu, H.; Shen, L. Y.; Fan, Y.; Zhang, P.; Chen, C. F.; Wang, W. X. Tetrahedron 2007, 63, 2404-2408.
http://dx.doi.org/10.1016/j.tet.2007.01.015

[23]. Cheng, L.; Wu, X.; Lu, Y. Org. Biomol. Chem. 2007, 5, 1018-1020.
http://dx.doi.org/10.1039/b701579h

[24]. Azizi, N.; Torkiyan, L.; Saidi, M. R. Org. Lett. 2006, 8, 2079-2082.
http://dx.doi.org/10.1021/ol060498v
PMid:16671786

[25]. Hayashi, Y.; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208-11209.
http://dx.doi.org/10.1021/ja0372513
PMid:16220937

[26]. Tomalia, D. A. In Polymer Chemistry A Practical Approach: Davis, F. J. Eds.; Oxford University Press: UK, 2004; pp. 188-194.

[27]. Tomalia, D. A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, G.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Polym. J. 1985, 17, 117-132.
http://dx.doi.org/10.1295/polymj.17.117

[28]. Lee, K. Y.; Kim, J. M.; Kim, J. N. Tetrahedron Lett. 2003, 44, 6737-6740.
http://dx.doi.org/10.1016/S0040-4039(03)01648-4

[29]. LeBlanc, R.; Dickson, J.; Brown, T.; Stewart, M.; Pati, H. N.; VanDerveer, D.; Arman, H.; Harris, J.; Pennington, W.; Holt, H. L. Jr.; Lee, M. Bioorg. Med. Chem. 2005, 13, 6025-6034.
http://dx.doi.org/10.1016/j.bmc.2005.06.028

[30]. Bhat, B. A.; Dhar, K. L.; Puri, S. C.; Saxena, A. K.; Shanmugavel, M.; Qazi, G. N. Bioorg. Med. Chem. Lett. 2005, 15, 3177-3180.
http://dx.doi.org/10.1016/j.bmcl.2005.03.121

[31]. Bhat, B. A.; Puri, S. C.; Qurishi, M. A.; Dhar, K. L.; Qazi, G. N. Synth. Commun. 2005, 35, 1135-1142.
http://dx.doi.org/10.1081/SCC-200054225

[32]. Abdon, I. M.; Saleh, A. M.; Zodhi, H. F. Molecules 2004, 9, 109-116.
http://dx.doi.org/10.3390/90300109
PMid:18007415

[33]. Straub, A.; Stasch, J.; Alonso-Alija, C.; Benet-Buchholz, J.; Ducke, B.; Feurer, A.; Furstner, C. Bioorg. Med. Chem. 2001, 11, 781-784.
http://dx.doi.org/10.1016/S0960-894X(01)00073-7

[34]. Ge, M.; Cline, E.; Yang, L. Tetrahedron Lett. 2006, 47, 5797-5799.
http://dx.doi.org/10.1016/j.tetlet.2006.05.173

[35]. Martins, M. A. P.; Cunico, W.; Siqueira, G. M.; Leidens, V. L.; Zanatta, N.; Bonacorso, H. G.; Flores, A. F. C. J. Braz. Chem. Soc. 2005, 16, 275-279.
http://dx.doi.org/10.1590/S0103-50532005000200022

[36]. Martins, M. A. B.; Beck, P.; Machado, P.; Brondani, S.; Moura, S.; Zanatta, N.; Bonacorso, H. G. B.; Flores, A. F. C. J. Braz. Chem. Soc. 2006, 17, 408-410.
http://dx.doi.org/10.1590/S0103-50532006000200027

[37]. Atlan, V.; Buron, C.; Kaim, L. E. Synlett 2000, 4, 489-490.

[38]. Soleiman, H. A.; Khalafallah, A. K.; Abd-Ellatif, H. Eur. J. Chem. 2012, 3(3), 316-321.
http://dx.doi.org/10.5155/eurjchem.3.3.316-321.612

[39]. Mohanty, M. K.; Sridhar, R.; Padmanavan, S. Y. Indian. J. Chem. 1977, 158, 1146-1148.

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