European Journal of Chemistry 2013, 4(2), 102-109 | doi: https://doi.org/10.5155/eurjchem.4.2.102-109.723 | Get rights and content

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Regioselective synthesis of some functionalized 3,4’-bis-(pyrazolyl)ketones and chemoselectivity in their reaction with hydrazine hydrate


Hamdi Mahmoud Hassaneen (1,*) , Ahmad Sami Shawali (2)

(1) Department of Chemistry, Faculty of Science, University of Cairo, Giza, 12613, Egypt
(2) Department of Chemistry, Faculty of Science, University of Cairo, Giza, 12613, Egypt
(*) Corresponding Author

Received: 16 Jan 2013 | Revised: 02 Feb 2013 | Accepted: 03 Feb 2013 | Published: 30 Jun 2013 | Issue Date: June 2013

Abstract


A new enamino ester, (E)-ethyl 3-(dipropylamino)acrylate, was prepared and used for synthesis of various pyrazole derivatives, 4a-k and 5a-d. Other new enaminone, (E)-ethyl 3-(3-(dimethylamino)acryloyl)-1-(4-nitrophenyl)-1H-pyrazole-4-carboxylate (8), was also prepared from compound 4a and utilized as precursor for synthesis of different functionalized 3,4'-bis-pyrazolyl ketones 9a-c, 10a-c. The site selectivity in hydrazinolysis of the latter was studied. The structures of the products namely pyrazolo[3,4-d]pyridazine derivatives 11(13) were confirmed by spectral and elemental analyses and by alternate unambiguous synthesis.

4_2_102_109

Keywords


Enaminones; Enamino esters; Regioselectivity; Chemoselectivity; Hydrazonoyl halides; Pyrazolo[3,4-d]pyridazines

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DOI: 10.5155/eurjchem.4.2.102-109.723

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[2]. Sobhi M. Gomha, Marwa S. ElGendy, Zeinab A. Muhammad, Abdou O. Abdelhamid, Marwa M. Abdel-Aziz
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[4]. Ahmad Sami Shawali
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DOI: 10.1016/j.jare.2016.09.001
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[5]. Hamdi M. Hassaneen, Tayseer A. Abdallah, Fatma M. Saleh, Yasmin Sh. Mohamed, Enas M. Awad
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[6]. Abdou O. Abdelhamid, Sobhi M. Gomha
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DOI: 10.1002/jhet.3485
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[7]. Magda F. Mohamed, Hamdi M. Hassaneen, Emad M. Elzayat, Salwa M. El-Hallouty, May El-Manawaty, Fatma M. Saleh, Yasmin Mohamed, Dina El-Zohiry, Ghada Fahmy, Nesma Abdelaal, Nouran Hassanin, Nouran Hossam
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Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Hassaneen, H.; Shawali, A. Eur. J. Chem. 2013, 4(2), 102-109. doi:10.5155/eurjchem.4.2.102-109.723
Hassaneen, H.; Shawali, A. Regioselective synthesis of some functionalized 3,4’-bis-(pyrazolyl)ketones and chemoselectivity in their reaction with hydrazine hydrate. Eur. J. Chem. 2013, 4(2), 102-109. doi:10.5155/eurjchem.4.2.102-109.723
Hassaneen, H., & Shawali, A. (2013). Regioselective synthesis of some functionalized 3,4’-bis-(pyrazolyl)ketones and chemoselectivity in their reaction with hydrazine hydrate. European Journal of Chemistry, 4(2), 102-109. doi:10.5155/eurjchem.4.2.102-109.723
Hassaneen, Hamdi, & Ahmad Sami Shawali. "Regioselective synthesis of some functionalized 3,4’-bis-(pyrazolyl)ketones and chemoselectivity in their reaction with hydrazine hydrate." European Journal of Chemistry [Online], 4.2 (2013): 102-109. Web. 13 Apr. 2021
Hassaneen, Hamdi, AND Shawali, Ahmad. "Regioselective synthesis of some functionalized 3,4’-bis-(pyrazolyl)ketones and chemoselectivity in their reaction with hydrazine hydrate" European Journal of Chemistry [Online], Volume 4 Number 2 (30 June 2013)

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