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Year 2022, Volume: 50 Issue: 2, 157 - 162, 28.02.2022
https://doi.org/10.15671/hjbc.954044

Abstract

References

  • Referans 1. R. Alam, D. Wahi, R. Singh, D. Sinha, V. Tandon, A. Grover, Rahusiddin, Design, synthesis, cytotoxicity, HuTopoIIa inhibitory activity and molecular docking studies of pyrazole derivatives as potential anticancer agents, Bioorg. Chem., 69 (2016) 77-90.
  • Referans 2. O. Rosati, M. Curini, M. C. Marcotullio, A. Macchiarulo, M. Perfumi, L. Mattioli, F. Rismondo, G. Cravotto, Synthesis, docking studies and anti-inflammatory activity of 4,5,6,7-tetrahydro-2H-indazole derivatives, Bioorgan. Med. Chem., 15 (2007) 3463-3473.
  • Referans 3. A. Bazgir, M. M. Khanaposhtani, A. A. Soorki, One-pot synthesis and antibacterial activities of pyrazolo[4’,3’:5,6]pyrido[2,3-d]pyrimidine-dione derivatives, Bioorg. Med. Chem. Lett, 18 (2008) 5800-5803.
  • Referans 4. M. Abdel-Aziz, G. E.-D. A. Abuo-Rahma, A. A. Hassan, Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities, Eur. J. Med. Chem., 44 (2009) 3480-3487.
  • Referans 5. D. Zampieri, M. G. Mamolo, E. Laurini, G. Scialino, E. Banfi, L. Vio, Antifungal and antimycobacterial activity of 1-(3,5-diaryl-4,5-dihydro-1H-pyrazol-4-yl)-1H-imidazole derivatives, Bioorgan. Med. Chem., 16 (2008) 4516-4522.
  • Referans 6. O. I. El-Sabbagh, M. M. Baraka, S. M. Ibrahim, C. Pannecouque, G. Andrei, R. Snoeck, J. Balzarini, A. A. Rashad, Synthesis and antiviral activity of new pyrazole and thiazole derivatives, Eur. J. Med. Chem., 44 (2009) 3746-3753.
  • Referans 7. J. S. M. Pasin, A. P. O. Ferreira, A. L. L. Saraiva, V. Ratzlaff, R. Andrighetto, P. Machado, S. Marchesan, R. A. Zanette, H. G. Bonacorso, N. Zanatta, M. A. P. Martins, J. Ferreira, C. F. Mello, Antipyretic and antioxidant activities of 5-trifluoromethyl-4,5-dihydro-1H-pyrazoles in rats, Braz. J. Med. Biol. Res., 43 (2010) 1193-1202.
  • Referans 8. Y. Ohtsuka, D. Uraguchi, K. Yamamoto, K. Tokuhisa, T. Yamakawa, Syntheses of 2-(trifluoromethyl)-1,3-dicarbonyl compounds through direct trifluoromethylation with CF3I and their application to fluorinated pyrazoles syntheses, Tetrahedron, 68 (2012) 2636-2649.
  • Referans 9. F. Gosselin, P. D. O’Shea, R. A. Webster, R. A. Reamer, R. D. Tillyer, E. J. J. Grabowski, Highly Regioselective Synthesis of 1-Aryl-3,4,5-Substituted Pyrazoles, Synlett, 9 (2006) 3267-3270.
  • Referans 10. B C. Bishop, K. M. J. Brands, A. D. Gibb, D. J. Kennedy, Regioselective Synthesis of 1,3,5-Substituted Pyrazoles from Acetylenic Ketones and Hydrazines, Synthesis, 1 (2004) 0043-0052.
  • Referans 11. Y. Ding, T. Zhang, Q.-Y. Chen, C. Zhu, Visible-Light Photocatalytic Aerobic Annulation for the Green Synthesis of Pyrazoles, Org. Lett., 17, 18 (2016) 4206-4209.
  • Referans 12. A. Alizedah, L. Moafi, L.-G. Zhu, Synthesis of fully substituted pyrazoles via regioselective 1,3‑dipolar cycloaddition reaction, J. Iran. Chem. Soc., 15 (2018) 1255-1259.
  • Referans 13. T. V. Baiju, I. N. N. Namboothiri, Synthesis of Functionalized Pyrazoles via 1,3-Dipolar Cycloaddition of -Diazo--ketophosphonates, Sufones and Esters with Electron-Deficient Alkenes, Chem. Rec, 17, (2017) 1-18.
  • Referans 14. G. W. Kabalka, L. H. M. Guindi, Selected .reductions of Conjugated Nitroalkenes, Tetrahedron, 46 (21) (1990) 7443-7457.
  • Referans 15. P. K. Pradhan, S. Dey, P. Jaisankar, V. S. Giri, Fe‐HCl: An Efficient Reagent for Deprotection of Oximes as well as Selective Oxidative Hydrolysis of Nitroalkenes and Nitroalkanes to Ketones, Synth. Commun., 35 (2005) 913-922.
  • Referans 16. L. Gottlieb, A. Hassner, H. E. Gottlieb, Stannous Chloride Reduction of Nitroalkenes in Amines. Synthesis and Cycloaddition of α-Dialkylaminoaldoxime, Synth. Commun., 30 (2000) 2445-2464.
  • Referans 17. T. Okino, Y. Hoashi, Y. Takemoto, Enantioselective Michael Reaction of Malonates to Nitroolefins Catalyzed by Bifunctional Organocatalysts, J. Am. Chem. Soc., 125 (2003) 12672-12673.
  • Referans 18. R. Kowalczyk, A. E. Nowak, J. Skarzewski, Organocatalytic asymmetric addition of aliphatic thiols to nitro olefins and nitrodienes, Tetrahedron: Asymm., 24 (2013) 505-514.
  • Referans 19. S.-J. Hong, M.-H. Lee, C.-H. Lee, meso-Substituted Dipyrromethanes from Vinylogous Aromatic Heterocycles and Their Utilization to the Synthesis of meso-Functionalized Porphyrins, Bull. Korean Chem. Soc., 25 (2004) 1545-1550.
  • Referans 20. A. Abdelwaly, I. Salama, M. S. Gomaa, M. A. Helal, Discovery of tetrahydro-ß-carboline derivatives as a new class of phosphodiesterase 4 inhibitors, Med. Chem. Res., 26 (2017) 3173-3187.

Synthesis of New Pyrazole Compounds via Diketonic Michael Adducts

Year 2022, Volume: 50 Issue: 2, 157 - 162, 28.02.2022
https://doi.org/10.15671/hjbc.954044

Abstract

Pyrazole ring containing heterocyclic molecules have been known to show biological activity. In this work, by realizing the cyclization reactions of diketonic Michael adducts, synthesis of new pyrazole compounds was accomplished. Diketonic Michael adducts were prepared in low-good yields by the addition reactions of acetylacetone to nitrovinyl arene compounds in the presence of piperidine. Pyrazole compounds were obtained in high yields via the cyclization reactions of these molecules. Structures of all the addition and the cyclization products were clarified by using 1H NMR, 13C NMR and HRMS techniques.

References

  • Referans 1. R. Alam, D. Wahi, R. Singh, D. Sinha, V. Tandon, A. Grover, Rahusiddin, Design, synthesis, cytotoxicity, HuTopoIIa inhibitory activity and molecular docking studies of pyrazole derivatives as potential anticancer agents, Bioorg. Chem., 69 (2016) 77-90.
  • Referans 2. O. Rosati, M. Curini, M. C. Marcotullio, A. Macchiarulo, M. Perfumi, L. Mattioli, F. Rismondo, G. Cravotto, Synthesis, docking studies and anti-inflammatory activity of 4,5,6,7-tetrahydro-2H-indazole derivatives, Bioorgan. Med. Chem., 15 (2007) 3463-3473.
  • Referans 3. A. Bazgir, M. M. Khanaposhtani, A. A. Soorki, One-pot synthesis and antibacterial activities of pyrazolo[4’,3’:5,6]pyrido[2,3-d]pyrimidine-dione derivatives, Bioorg. Med. Chem. Lett, 18 (2008) 5800-5803.
  • Referans 4. M. Abdel-Aziz, G. E.-D. A. Abuo-Rahma, A. A. Hassan, Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities, Eur. J. Med. Chem., 44 (2009) 3480-3487.
  • Referans 5. D. Zampieri, M. G. Mamolo, E. Laurini, G. Scialino, E. Banfi, L. Vio, Antifungal and antimycobacterial activity of 1-(3,5-diaryl-4,5-dihydro-1H-pyrazol-4-yl)-1H-imidazole derivatives, Bioorgan. Med. Chem., 16 (2008) 4516-4522.
  • Referans 6. O. I. El-Sabbagh, M. M. Baraka, S. M. Ibrahim, C. Pannecouque, G. Andrei, R. Snoeck, J. Balzarini, A. A. Rashad, Synthesis and antiviral activity of new pyrazole and thiazole derivatives, Eur. J. Med. Chem., 44 (2009) 3746-3753.
  • Referans 7. J. S. M. Pasin, A. P. O. Ferreira, A. L. L. Saraiva, V. Ratzlaff, R. Andrighetto, P. Machado, S. Marchesan, R. A. Zanette, H. G. Bonacorso, N. Zanatta, M. A. P. Martins, J. Ferreira, C. F. Mello, Antipyretic and antioxidant activities of 5-trifluoromethyl-4,5-dihydro-1H-pyrazoles in rats, Braz. J. Med. Biol. Res., 43 (2010) 1193-1202.
  • Referans 8. Y. Ohtsuka, D. Uraguchi, K. Yamamoto, K. Tokuhisa, T. Yamakawa, Syntheses of 2-(trifluoromethyl)-1,3-dicarbonyl compounds through direct trifluoromethylation with CF3I and their application to fluorinated pyrazoles syntheses, Tetrahedron, 68 (2012) 2636-2649.
  • Referans 9. F. Gosselin, P. D. O’Shea, R. A. Webster, R. A. Reamer, R. D. Tillyer, E. J. J. Grabowski, Highly Regioselective Synthesis of 1-Aryl-3,4,5-Substituted Pyrazoles, Synlett, 9 (2006) 3267-3270.
  • Referans 10. B C. Bishop, K. M. J. Brands, A. D. Gibb, D. J. Kennedy, Regioselective Synthesis of 1,3,5-Substituted Pyrazoles from Acetylenic Ketones and Hydrazines, Synthesis, 1 (2004) 0043-0052.
  • Referans 11. Y. Ding, T. Zhang, Q.-Y. Chen, C. Zhu, Visible-Light Photocatalytic Aerobic Annulation for the Green Synthesis of Pyrazoles, Org. Lett., 17, 18 (2016) 4206-4209.
  • Referans 12. A. Alizedah, L. Moafi, L.-G. Zhu, Synthesis of fully substituted pyrazoles via regioselective 1,3‑dipolar cycloaddition reaction, J. Iran. Chem. Soc., 15 (2018) 1255-1259.
  • Referans 13. T. V. Baiju, I. N. N. Namboothiri, Synthesis of Functionalized Pyrazoles via 1,3-Dipolar Cycloaddition of -Diazo--ketophosphonates, Sufones and Esters with Electron-Deficient Alkenes, Chem. Rec, 17, (2017) 1-18.
  • Referans 14. G. W. Kabalka, L. H. M. Guindi, Selected .reductions of Conjugated Nitroalkenes, Tetrahedron, 46 (21) (1990) 7443-7457.
  • Referans 15. P. K. Pradhan, S. Dey, P. Jaisankar, V. S. Giri, Fe‐HCl: An Efficient Reagent for Deprotection of Oximes as well as Selective Oxidative Hydrolysis of Nitroalkenes and Nitroalkanes to Ketones, Synth. Commun., 35 (2005) 913-922.
  • Referans 16. L. Gottlieb, A. Hassner, H. E. Gottlieb, Stannous Chloride Reduction of Nitroalkenes in Amines. Synthesis and Cycloaddition of α-Dialkylaminoaldoxime, Synth. Commun., 30 (2000) 2445-2464.
  • Referans 17. T. Okino, Y. Hoashi, Y. Takemoto, Enantioselective Michael Reaction of Malonates to Nitroolefins Catalyzed by Bifunctional Organocatalysts, J. Am. Chem. Soc., 125 (2003) 12672-12673.
  • Referans 18. R. Kowalczyk, A. E. Nowak, J. Skarzewski, Organocatalytic asymmetric addition of aliphatic thiols to nitro olefins and nitrodienes, Tetrahedron: Asymm., 24 (2013) 505-514.
  • Referans 19. S.-J. Hong, M.-H. Lee, C.-H. Lee, meso-Substituted Dipyrromethanes from Vinylogous Aromatic Heterocycles and Their Utilization to the Synthesis of meso-Functionalized Porphyrins, Bull. Korean Chem. Soc., 25 (2004) 1545-1550.
  • Referans 20. A. Abdelwaly, I. Salama, M. S. Gomaa, M. A. Helal, Discovery of tetrahydro-ß-carboline derivatives as a new class of phosphodiesterase 4 inhibitors, Med. Chem. Res., 26 (2017) 3173-3187.
There are 20 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Articles
Authors

Seda Çınar 0000-0001-6591-7141

Aslı Eren This is me 0000-0001-8184-8094

Publication Date February 28, 2022
Acceptance Date December 24, 2021
Published in Issue Year 2022 Volume: 50 Issue: 2

Cite

APA Çınar, S., & Eren, A. (2022). Synthesis of New Pyrazole Compounds via Diketonic Michael Adducts. Hacettepe Journal of Biology and Chemistry, 50(2), 157-162. https://doi.org/10.15671/hjbc.954044
AMA Çınar S, Eren A. Synthesis of New Pyrazole Compounds via Diketonic Michael Adducts. HJBC. February 2022;50(2):157-162. doi:10.15671/hjbc.954044
Chicago Çınar, Seda, and Aslı Eren. “Synthesis of New Pyrazole Compounds via Diketonic Michael Adducts”. Hacettepe Journal of Biology and Chemistry 50, no. 2 (February 2022): 157-62. https://doi.org/10.15671/hjbc.954044.
EndNote Çınar S, Eren A (February 1, 2022) Synthesis of New Pyrazole Compounds via Diketonic Michael Adducts. Hacettepe Journal of Biology and Chemistry 50 2 157–162.
IEEE S. Çınar and A. Eren, “Synthesis of New Pyrazole Compounds via Diketonic Michael Adducts”, HJBC, vol. 50, no. 2, pp. 157–162, 2022, doi: 10.15671/hjbc.954044.
ISNAD Çınar, Seda - Eren, Aslı. “Synthesis of New Pyrazole Compounds via Diketonic Michael Adducts”. Hacettepe Journal of Biology and Chemistry 50/2 (February 2022), 157-162. https://doi.org/10.15671/hjbc.954044.
JAMA Çınar S, Eren A. Synthesis of New Pyrazole Compounds via Diketonic Michael Adducts. HJBC. 2022;50:157–162.
MLA Çınar, Seda and Aslı Eren. “Synthesis of New Pyrazole Compounds via Diketonic Michael Adducts”. Hacettepe Journal of Biology and Chemistry, vol. 50, no. 2, 2022, pp. 157-62, doi:10.15671/hjbc.954044.
Vancouver Çınar S, Eren A. Synthesis of New Pyrazole Compounds via Diketonic Michael Adducts. HJBC. 2022;50(2):157-62.

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