OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS
Synthesis and characterization of novel pyrazolone derivatives
Magda Ismail Marzouk (1,*) , Galal Hosni Sayed (2) , Mohamed Said Abd ElHalim (3) , Salma Yehia Mansour (4)
(1) Heterocyclic Synthetic Laboratory, Chemistry Department, Faculty of Science, Ain Shams University, Abbassia 11566, Cairo, Egypt
(2) Heterocyclic Synthetic Laboratory, Chemistry Department, Faculty of Science, Ain Shams University, Abbassia 11566, Cairo, Egypt
(3) Heterocyclic Synthetic Laboratory, Chemistry Department, Faculty of Engineering, Ain Shams University, Abbassia 11566, Cairo, Egypt
(4) Heterocyclic Synthetic Laboratory, Chemistry Department, Faculty of Science, Ain Shams University, Abbassia 11566, Cairo, Egypt
(*) Corresponding Author
Received: 10 Jul 2013 | Accepted: 26 Aug 2013 | Published: 31 Mar 2014 | Issue Date: March 2014
The reactivity of hydrogen atoms at C-4 of pyrazolone 3 towards condensation reactions was studied by its reaction with p-anisaldehyde, malononitrile and/or ethyl acetoacetate in the presence of ammonium acetate and/or piperidine, glucose, phenyl isothiocyanate, 2-amino thiazole and aniline to afford compounds 4-6, 13, 15, 17 and 18, respectively. Reaction of amino carbonitrile 4 with ammonium thiocyanate, and formamide afforded compound 7 and pyrazolo[3,4-b]pyridinylformamide, 9. Reaction of compound 7 with hydrazine hydrate gave thiocyanato-1,3,4-thiadiazol-2-yl)-1H-pyrazolo[3,4-b]pyridin-6-amine derivative, 8. Acetylation of amino carbonitriles 4 and 5 afforded compound 10 and 11, respectively. Reaction of compound 11 with hydrazine hydrate afforded azanediyl compound 12. The pyrazolone 19 reacted with different nitrogen nucleophiles such as hydrazine hydrate, urea, thiourea and hydroxylamine hydrochloride to afford compounds 22-25. The reactivity of pyrazolone 19 as an α,β-unsaturated compound towards several carbon nucleophiles under Michael reaction was studied by its reaction with ethyl acetoacetate, ethyl cyanoacetate, and malononitrile under different reaction conditions and pyrazolone 3 to afford compounds 26-32, respectively. Synthesis of amino carbonitriles 5, pyrazolone 19 and pyrazolo[3,4-c]pyrazole 22 were carried out under microwave irradiation. The newly synthesized compounds were characterized by IR, 1H NMR and mass spectral data.
Links for Article
| | | | | | |
| | | | | | |
Article MetricsThis Abstract was viewed 1660 times | PDF Article downloaded 915 times
Department of Chemistry, Faculty of Science, Ain Shams University, Cairo, Egypt
. Sundaravel Vivek Kumar, Shanmugam Muthusubramanian, Subbu Perumal
Recent Progress in the Synthesis of Pyrazolopyridines and Their Derivatives
Organic Preparations and Procedures International 51(1), 1, 2019
. Kumar, L.; Thakur, C.; Sharma, V. Int. J. Res. Pharm. Sci. 2012, 2, 13-22
. Halen, P. K.; Murumkar, P.; Giridhar, R.; Yadav, M. R. Mini-Rev. Med. Chem. 2009, 9, 124-139.
. Kucukguzel, G.; Rollas, S.; Erdeniz, H.; Kiraz, M.; Ekinci, A.; Cevdet, V. A. Eur. J. Med. Chem. 2000, 35, 761-771.
. Mariappan, G.; Saha, B. P.; Sutharson, L.; Ankit, Garg, S. Pandey, L. Kumar, D. J. Pharm. Res. 2010, 3, 2856-2859.
. Devnath, H. P.; Islam, M. R. Bangladesh J. Pharmacol. 2010, 5, 30-33.
. Rahat, K.; Imam, U.; Alam, M.; Sultan, D. Bangladesh J. Pharmacol. 2008, 3, 27-35.
. Soni, J. P.; Sen, D. J.; Modh, K. M. J. Appl. Pharm. Sci. 2011, 1, 115-120.
. Sunitha, S.; Aravindakshan, K. K. Int. J. Pharm. Bio. Sci. 2011, 2, 108-113.
. Vijesh, A. M.; Arun, M. I.; Shrikrishna, I.; Shivananda, K. N.; Shyma, P. C.; Arulmoli, T. Der Pharma Chem. 2011, 3, 454-463.
. Kumar, K. S.; Rajasekharan, A. Int. J. Res. Pharm. Chem. 2012, 2, 327-337.
. Evstropov, A. N.; Yavorovskaya, V. E.; Vorobev, E. S.; Khudonogova, Z. P.; Medvedeva, S. G.; Filimonov, V. D.; Prishchep, T. P.; Saratikov, A. S. Pharm. Chem. J. 1992, 26, 426-430.
. Nirupam, D.; Abilasha, V.; Shrivastava, K.; Shrivastva, P.; Sushant, K. Indian J. Chem. B 2008, 47, 1555-1558.
. Amir, M.; Shikha, K. Indian J. Chem. B 2005, 44, 2532-2537.
. Ragab, F. A.; Abdel-Gawad, N. M.; Georgey, H. H.; Said, M. F. Chem. Pharm. Bull. 2013, 61(8), 834-845.
. Al-Mutairi, A. A.; El-Baih, F. E. M.; Al-Hazimi, H. M. J. Saudi Chem. Soc. 2010, 14, 287-299.
. Cooper, R. E.; Kavanageh, F. W. Analytical Microbiology, Vol. I and II, Academic press: New York and London, 1972.
. Vogel, A. I. Elementary Practical Organic Chemistry Part II, Qualitative Organic Analysis, 2nd edition, Longman, London 1966.
. Abdel-Fattah, A. M.; Sherif, S. M.; El-Reedy, A. M.; Gad-Alla, S. A. Phosphorus Sulfur 1992, 70, 67-73.
. Khalil, M. A.; Sayed, S. M.; Raslan, M. A. Am. J. Org. Chem. 2012, 2, 161-170.
How to cite
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.5.1.24-32.870
| | | | | | |
| | | | | |
Save to Zotero Save to Mendeley
European Journal of Chemistry 2014, 5(1), 24-32 | doi: https://doi.org/10.5155/eurjchem.5.1.24-32.870 | Get rights and content
- There are currently no refbacks.
© Copyright 2010 - 2020 • Atlanta Publishing House LLC • All Right Reserved.
The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.
Copyright 2010-2020 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.