PİRAZOL TÜREVLERİNİN SENTEZ METODLARI

Adnan Çetin

doi:10.18586/msufbd.93870

PİRAZOL TÜREVLERİNİN SENTEZ METODLARI

Abstract

Bu derlemede pirazollerin sentez süreçlerini incelemek hedeflenmiştir. Heterosiklik bileşiklerin önemli bir sınıfını oluşturan pirazoller biyoaktif özelliklerinden dolayı geniş bir çalışma alanı olarak önemi artarak devam etmektedir. Pirazoller biyolojik aktif çeşitliliğine sahiptir. Bu bileşikler ilaç araştırmalarında ve tarım ürünleri geliştirmesinde kullanılmaktadır. Böylece pirazollerin sentezi için geliştirilmiş metotlar daha önemli hale gelmektedir.

Keywords

Anahtar Kel meler: Heterosiklik kimya, organik kimya, organik sentez, pirazol

References

Behr, L. C., Fusco, R., Jarboe, C. H. The Chemistry of Heterocyclic Compounds: Pyrazoles, Pyrazolines, Pyrazolidines, Inzadoles and Condensed Rings, Wiley and Sons: London, 1967.
Sharp, A. J. The Journal of Ecology, 374-380, 1953.
Wiley, R. H. The Chemistry of Heterocyclic Chemistry: Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings, Behr, L. C., Fusco, R., Jarboe, C. H., Interscience Publishers: John Wiley & Sons, 3-20, 1967.
Eicher T., Hauptmann, S. The Chemistry of Heterocycles: Structure, Reactions, Synthesis, and Applications, Wiley-VCH, Weinheim, 179, 2003.
Fustero, S., Sanchez-Rosello, M., Barrio, P., Simon-Fuentes, A., Chem. Rev. 111, 6984–7034, 2011.
Gerstenberger, B. S.; Rauckhorst, M. R.; Starr, J. T. Org. Lett. 11, 2097, 2009.
Zhu, Y., Hong, J. J., Zhou, Y. B., Xiao, Y. W., Lin, M., Zhan, Z. P. Selective synthesis of 4-(sulfonyl)-methyl-1 H-pyrazoles and (E)-4, 5-dihydro-1 H-pyrazoles from N-allenic sulfonylhydrazones. Organic & biomolecular chemistry, 12(23), 3797, 2014.
Yet, L. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R., Ramsden, C. A., Scriven, E. F. V., Taylor, R. J. K. Eds.; Elsevier: Oxford, U.K, (4),1, 2008.

Ablajan, K., Liju, W., Kelimu, Y., Jun, F. Cerium ammonium nitrate (CAN)-catalyzed four-component one-pot synthesis of multi-substituted pyrano [2, 3- varvec {c}] pyrazoles under ultrasound irradiation. Molecular diversity, 17(4), 693, 2013.
Lévai, A., Silva, A. M. S., Cavaleiro, J. A. S., Alkorta, I., Elguero, J. Ve Jeko, J. Synthesis of Pyrazoles by Treatment of 3-Benzylchromones, 3- Benzylflavones and Their 4-Thio Analogues with Hydrazine, Eur. J. Org. Chem., 12, 2825–2832, 2006.
Singh, S. R., Kumar, D., Batra, H., Naithani, R., Rozas, I., Elguero, J. Can. J. Chem. 78, 1109, 2000.
Heler, S. T., ve Natarajan, S. R. 1,3-Diketones from Acid Chlorides and Ketones: A Rapid and General One-Pot Synthesis of Pyrazoles, Organic Letters, 8, 2675-2678, 2006.
Gosselin, F., O’Shea, P. D., Webster, R. A., Reamer, R. A., Tillyer, R. D., Grabowski, E. J. J. Synlett,19, 3267, 2006.
Wang, Z.-X., Qin, H.-L, Green Chem., 6, 90, 2004.
Minutolo, F., Macchia, M., Katzenellenbogen, B. S., Katzenellenbogen, J. A. Estrogen receptor β ligands: recent advances and biomedical applications. Medicinal research reviews, 31(3), 364, 2011.
Stauffer, S. R., Coletta, C. J., Tedesco, R., Nishiguchi, G., Carlson, K., Sun, J., Katzenellenbogen, B. S., Katzenellenbogen, J. A. J. Med. Chem., 43 (26), 4934 -4947, 2000.
Hote, B. S., Lokhande, P. D. Novel and Efficient Synthesis of 4-Indazolyl-1, 3, 4-trisubstituted Pyrazole Derivatives. Synthetic Communications, 44(10), 1492-1500, 2014.
Sun, J., Huang, Y. R., Harrington, W. R., Sheng, S., Katzenellenbogen, J. A., Katzenellenbogen, B. S. Antagonists selective for estrogen receptor α. Endocrinology, 143(3), 941-947, 2002.
Ma, W., Peterson, B., Kelson, A., Laborde, E. Efficient Synthesis of Trisubstituted Pyrazoles and Isoxazoles Using a Traceless “Catch and Release” Solid-Phase Strategy. Journal of combinatorial chemistry, 11(4), 697, 2009.
Huang, S., Lin, R., Yu, Y., Lu, Y., Connolly, P. J., Chiu, G., Li, S., Emanuel, S. L., Middleton, S. A. Bioorg. Med. Chem. Lett. 17, 1243-48, 2007.
Polshettiwar, V., Varma, R. S., Greener and rapid access to bio-active heterocycles: room temperature synthesis of pyrazoles and diazepines in aqueous medium, Tetrahedron Letters, 49, 397-400, 2008.
Chen, X., She, J., Shang, Z., Wu, J., Wu, H., Zhang, P. One pot synthesis and biological activity of 2,5- dipyrazolyl-1,3,4-oxadiazoles, Synthesis. 3478, 2008.
Devery, J. J., Mohanta, P. K., Casey, B. M., Flowers, R. A. Synlett. 1490, 2009.
Wang, D.-J., Fan, L., Zheng, C.-Y., Fang, Z.-D. J. Fluorine Chem. 131, 584. 2010.
Montoya, V., Pons, J., García-Anton, J., Solans, X., Font-Bardia, M., Ros, J. J. Fluorine Chem. 128, 1007, 2007.
Dai, H., Yu, H.-B., Liu, J.-B., Li, Y.-Q., Qin, X.; Zhang, X., Qin, Z.-F., Wang, T.-T., Fang, J.-X. Arkivoc, 126, 2009.
Samshuddin, S., Narayana, B., Sarojini, B. K., Srinivasan, R., Vinayachandra, C. K. Synthesis, characterization and biological evaluation of some pyrazoles derived from α, β-dibromo 4, 4′-difluoro chalcone, Der Pharma Chemica, 4(2), 587, 2012.
Shavnya, A., Sakya, S. M., Munich, M. L., Rast, B., DeMello, K. L., Jaynes, B. H. Tetrahedron Lett., 46, 6887, 2005.
Janin, Y. L. Org. Chem. 7, 314, 2010.
Guillou, S., Janin, Y. L. Chem.—Eur. J. 16, 4669, 2010.
Guillou, S., Bonhomme, F. J., Janin, Y. L. Synthesis., 3504, 2008.
Mert, S., Kasımoğulları, R., Iça, T., Çolak, F., Altun, A., Ok, S. Synthesis, structure–activity relationships, and in vitro antibacterial and antifungal activity evaluations of novel pyrazole carboxylic and dicarboxylic acid derivatives. European journal of medicinal chemistry, 78, 86-96, 2014.
Katoch-Rouse, R., Pavlova, O. A., Caulder, T., Hoffman, A. F., Mukhin, A. G., Horti, A. G. J. Med. Chem. 46, 642, 2003,
Finn, J., Mattia, K., Morytko, M., Ram, S., Yang, Y., Wu, X. Mak, E., Gallant, P., Kith, D. Bioorg. Med. Chem. Lett. 13, 2231, 2003.
Bildirici, İ., Şener, A., Atalan, E., Battal, A., Genç, H. Synthesis and antibacterial activity of 4-benzoyl-1-(4-carboxy-phenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid and derivatives. Medicinal chemistry research, 18(5), 327, 2009.
Ranatunge, R. R., Augustyniak, M., Bandarage, U. K., Earl, R. A., Ellis, J. L., Garvey, D. S.,Janero, D. R., Letts, L. G., Martino, A. M., Murty,M. G., Richardson, S. K., Schroeder, J. D., Shumway,M. J., Tam, S. W.,Trocha, A. M., Young, D. V. J. Med. Chem. 47, 2180, 2004.
Huang, S., Lin, R., Yu, Y., Lu, Y., Connolly, P. J., Chiu, G., Li, S., Emanuel, S. L., Middleton, S. A. Bioorg. Med. Chem. Lett. 17, 1243, 2007.
Prakash, O., Sharma, D., Kamal, R., Kumar, R., Nair, R. R. Tetrahedron 65, 10175, 2009.
Aggarwal, R., Kumar, V., Singh, S. P. Indian J. Chem. 46B, 1332, 2007.
Ponnala, S., Sahu, D. P. Synth. Commun. 36, 2189, 2006.
Bhat, B. A., Puri, S. C., Qurishi, M. A., Dhar, K. L., Qazi, G. N. Synth. Commun., 35, 1135-1142, 2005.
Nikpour, F., Beigvand, M. Monatsh. Chem. 139, 821, 2008.
Katritzky, A. R., Wang, M., Zhang, S., Voronkov, M. V. J. Org. Chem., 66, 6787, 2001.
Shao, N., Chen, T., Zhang, T., Zhu, H., Zheng, Q., Zou, H. Cascade regioselective synthesis of pyrazoles from nitroallylic acetates and N-tosyl hydrazine. Tetrahedron, 70(4), 795, 2014.
Adlington, R. M., Baldwin, J. E., Catterick, D., Pritchard, G. J., Tang, L. T. J. Chem. Soc., Perkin Trans. 1 15, 2311, 2000.
Kirkham, J. D., Edeson, S. J., Stokes, S., Harrity, J. P. Synthesis of ynone trifluoroborates toward functionalized pyrazoles. Organic letters, 14(20), 5354, 2012.
Chandanshive, J. Z., González, P. B., Tiznado, W., Bonini, B. F., Caballero, J., Femoni, C., Franchini, M. C. 1, 3-Dipolar cycloaddition of nitrile imines with α, β-unsaturated lactones, thiolactones and lactams: synthesis of ring-fused pyrazoles. Tetrahedron, 68(16), 3319, 2012.
Bagley, M. C.,Lubinu, M. C., Mason, C. Synlett. 704, 2007.
Pinto, D. C .G. A., Silva, A. M. S., Cavaleiro, J. A. S., Elguero, J. Eur. J. Org. Chem. 747, 2003.
Abdel-Wahaba, B. F., Dawoodb, K. M. Synthesis and applications of bipyrazole systems. Arkivoc, 1, 491, 2012.
Elguero, J., Silva, A., Tome, A. C. Five‐Membered Heterocycles: 1, 2‐Azoles. Part 1. Pyrazoles. Modern heterocyclic chemistry, 635, 2011.
Lévai, A., Silva, A. M. S., Cavaleiro, J. A. S., Alkorta, I., Elguero, J. Ve Jeko, J. Eur. J. Org. Chem., 2825, 2006.
Dymock, B. W., Barril, X., Brough, P. A., Cansfield, J. E., Massey, A., McDonald, E., Hubbard, R. E., Surgenor, A., Roughley, S. D., Webb, P., Workman, P., Wright, L., Drysdale, M. J. J. Med. Chem. 48, 4212, 2005.
Yadav, J. S., Reddy, B. V. S., Satheesh, G., Lakshmi, P. N., Kumar, S. K., Kunwar, A. C. Tetrahedron Lett. 45, 8587, 2004.
Molteni, V., Hamilton, M. M., Mao, L., Crane, C. M., Termin, A. P., Wilson, D. M. Synthesis, 1669, 2002.
Kennedy, L. J. Synlett, 600, 2008.
Dewang, P. M., Kim, D.-K. Bioorg. Med. Chem. Lett. 20, 4228, 2010.
Park, B. S., El-Deeb, I. M., Yoo, K. H., Oh, C.-H., Cho, S. J., Han, D. K., Lee, H.-S., Lee, J. Y., Lee, S. H. Bioorg. Med. Chem. Lett. 19, 4720, 2009.
Juneja, H., Panchbhai, D., Sheikh, J., Ingle, V, Hadda, T. B. Synthesis, antibacterial screening, and POM analyses of novel bis-isoxazolyl/pyrazolyl-1, 3-diols. Medicinal Chemistry Research, 23(3), 1537, 2014.
Longhi, K., Moreira, D. N., Marzari, M. R. B., Floss, V. M., Bonacorso, H. G., Zanatta, N., Martins, M. A. P. Tetrahedron Lett. 51, 3193, 2010.
Persson, T., Nielsen, J. Org. Lett. 8, 3219, 2006.
Giacomelli, G., Porcheddu, A., Salaris, M.,Taddei, M. Eur. J. Org. Chem. 537, 2003.
Kralj, D., Friedrich, M., Groselj, U., Kiraly-Potpara, S., Meden, A., Wagger, J., Dahmann, G., Stanovnik, B., Svete, J., Tetrahedron 65, 7151, 2009.
Chun, Y. S., Lee, K. K., Ko, Y. O., Shin, H., Lee, S.-G. Chem. Commun. 5098, 2008.
Ko, Y. O., Chun, Y. C., Park, C.-L., Kim, Y., Shin, H.; Ahn, S., Hong, J., Lee, S.-G. Org. Biomol. Chem. 7, 1132, 2009.
Rai, N. S., Kalluraya, B., Lingappa, B., Shenoy, S., Puranic, V. G. Eur. J. Med. Chem. 43, 1715, 2008.
Martins, M.A.P., Pereira, C.M.P., Beck, P., Machado, P., Teixeira, M.V.M., Bonacorso, H.G. Zanatta, N. Tetrahedron Letters, 44, 6669, 2003.
Rosa, F. A., Machado, P., Vargas, P. S., Bonacorso, H. G., Zanatta, N., Martins, M. A. P. Synlett, 1673, 2008.
Mellor, J. M., Schofield, S. R., Korn, S. R. Tetrahedron, 53, 17151, 1997.
Elgemie, G. E. H., Elghandour, A. H., Ali, H. A., Hussein, A. M. Synth. Commun. 32, 2245, 2002.
Peruncheralathan, S., Khan, T. A., Ila, H., Junjappa, H. J. Org. Chem. 70, 10030, 2005.
Beltran-Rodil, S., Edwards, M. G., Pugh, D. S., Reid, M., Taylor, R. J. K. Synlett, 602, 2010.
Li, G., Kakarla, R., Gerritz, S. W. Tetrahedron Lett. 48, 4595, 2007.
Padwa, A. 1,3-Dipolar Cycloaddition Chemistry; J. Wiley and Sons: New York. 1984.
Polshettiwar, V., Varma, R. S. Greener and rapid access to bio-active heterocycles: room temperature synthesis of pyrazoles and diazepines in aqueous medium. Tetrahedron Letters, 49(2), 397, 2008.
Wu, L., Shi, M., J. Org. Chem. 75, 2296, 2010.
Hari, Y., Tsuchida, S., Sone, R., Aoyama, T. Synthesis, 3371, 2007.
Jiang, N., Li, C.-J. Chem. Commun. 394, 2004.
He, S., Chen, L., Niu, Y.-N., Wu, L.-Y., Liang, Y.-M. Tetrahedron Lett. 50, 2443, 2009.
Kissane, M., Lawrence, S. E., Maguire, A. R. Org. Biomol. Chem. 8, 2735, 2010.
Nair, V., Suja. T. D. Intramolecular 1, 3-dipolar cycloaddition reactions in targeted syntheses." Tetrahedron 63.50 12247, 2007.
Sui, Z., Guan, J., Ferro, M. P., McCoy, K., Walter, M. P., Murria, W. V., Singer, M., Steber, M., Ritchie, D. M., Argentieri, D. C. Bioorg. Med. Chem. Lett. 10, 601, 2000.
Donohue, S. R., Halldin, C., Pike, V. W. Tetrahedron Lett. 49, 2789, 2008.
Donohue, A. C., Pallich, S., McCarthy, T. D. J. Chem. Soc., Perkin Trans. 1, 2817, 2001.
Fuchi, N., Doi, T., Takahasi, T. Chem. Lett. 34, 438, 2005.
Dadiboyena, S., Valente, E. J., Hamme, A. T. Tetrahedron Lett. 51, 1341, 2010.
Chandanshive, J. Z., Bonini, B. F., Gentili, D., Fochi, M., Bernardi, L., Franchini, M. C. European Journal of Organic Chemistry, 33, 6440, 2010.
Conti, P., Pinto, A., Tamborini, L., Rizzo, V., De Micheli, C. Tetrahedron, 63, 5554, 2007.
Browne, D. L., Harrity, J. P. A. Recent developments in the chemistry of sydnones, Tetrahedron, 66, 553, 2010.
He, S., Chen, L., Niu, Y.-N., Wu, L.-Y., Liang, Y.-M. Tetrahedron Lett. 50, 2443, 2009.
Chang, E.-M., Chen, T.-H.,Wong, F. F., Chang, E.-C., Yeh, M.-Y. Synlett, 901, 2006.
Foster, R. S., Huang, J., Vivat, J. F., Browne, D. L., Harrity, J. P. A. Org. Biomol. Chem. 7, 4052, 2009.
Martín, R., Rodríguez-Rivero, M., Buchwald, S. L. Angew. Chem., Int. Ed. 45, 7079, 2006.
Hayes, S. J., Knight, D. W., O’Halloran, M., Pickering, S. R. Synlett. 2188, 2008.
Lee, Y. T., Chung, Y. K. J. Org. Chem. 73, 4698, 2008.
Liu, H.-L., Jiang, H.-F., Zhang, M., Yao, W.-J., Zhu, Q.-H., Tang, Z. Tetrahedron Lett. 49, 3805, 2008.
Willy, B., Muller, T. J. J. Eur. J. Org. Chem. 4157, 2008.
Ahamad, S., Gupta, A. K., Kant, R., Mohanan, K. Domino reaction involving the Bestmann–Ohira reagent and α, β-unsaturated aldehydes: efficient synthesis of functionalized pyrazoles. Organic Biomolecular chemistry, 13(5), 1492, 2015.
Stonehouse, J. P., Chekmarev, D. S., Ivanova, N. I., Lang, S., Pairaudeau, G., Smith, N., Stocks, M. J., Sviridov, S. I., Utkina, L. M. Synlett, 100, 2008.
Dömling, A. Chem. Rev. 106, 17, 2006.
Adib,M., Mohammadi, B., Bijanzadeh, H. R. Synlett, 3180, 2008.
Majumder, S., Gipson, K. R., Staples, R. J., Odom, A. L. Adv. Synth. Catal. 351, 2013, 2009.
Nair, V., Biju, A. T., Mohanan, K., Suresh, E. Organic Letters, 8, 2213, 2006.
Yavari, I., Khalili, G., Mirzaei, A. Helv. Chim. Acta, 93, 277, 2010.
Neumann, J. J., Suri, M., Glorius, F. Angew. Chem., Int. Ed. 49, 7790, 2010.
Suen, Y. F., Hope, H., Nantz, M. H., Haddadin, M. J., Kurth, M. J. J. Org. Chem. 70, 8468, 2005.
Dragovich, P. S., Bertolini, T. M., Ayida, B. K., Li, L.-S., Murphy, D. E., Ruebsam, F., Sun, Z., Zhou, Y. Tetrahedron, 63, 2007.

Details

Primary Language

Turkish

Subjects

-

Journal Section

-

Authors

Adnan Çetin

Publication Date

June 1, 2015

Submission Date

June 23, 2015

Acceptance Date

-

Published in Issue

Year 2015 Volume: 3 Number: 1

DOI

https://doi.org/10.18586/msufbd.93870

IZ

https://izlik.org/JA86ES94KK

Cite

RIS / Bibtex

APA

Çetin, A. (2015). PİRAZOL TÜREVLERİNİN SENTEZ METODLARI. Mus Alparslan University Journal of Science, 3(1), 303-321. https://doi.org/10.18586/msufbd.93870

AMA

1.Çetin A. PİRAZOL TÜREVLERİNİN SENTEZ METODLARI. Mus Alparslan University Journal of Science. 2015;3(1):303-321. doi:10.18586/msufbd.93870

Chicago

Çetin, Adnan. 2015. “PİRAZOL TÜREVLERİNİN SENTEZ METODLARI”. Mus Alparslan University Journal of Science 3 (1): 303-21. https://doi.org/10.18586/msufbd.93870.

EndNote

Çetin A (November 1, 2015) PİRAZOL TÜREVLERİNİN SENTEZ METODLARI. Mus Alparslan University Journal of Science 3 1 303–321.

IEEE

[1]A. Çetin, “PİRAZOL TÜREVLERİNİN SENTEZ METODLARI”, Mus Alparslan University Journal of Science, vol. 3, no. 1, pp. 303–321, Nov. 2015, doi: 10.18586/msufbd.93870.

ISNAD

Çetin, Adnan. “PİRAZOL TÜREVLERİNİN SENTEZ METODLARI”. Mus Alparslan University Journal of Science 3/1 (November 1, 2015): 303-321. https://doi.org/10.18586/msufbd.93870.

JAMA

1.Çetin A. PİRAZOL TÜREVLERİNİN SENTEZ METODLARI. Mus Alparslan University Journal of Science. 2015;3:303–321.

MLA

Çetin, Adnan. “PİRAZOL TÜREVLERİNİN SENTEZ METODLARI”. Mus Alparslan University Journal of Science, vol. 3, no. 1, Nov. 2015, pp. 303-21, doi:10.18586/msufbd.93870.

Vancouver

1.Adnan Çetin. PİRAZOL TÜREVLERİNİN SENTEZ METODLARI. Mus Alparslan University Journal of Science. 2015 Nov. 1;3(1):303-21. doi:10.18586/msufbd.93870