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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.
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DOI: 10.5155/eurjchem.4.2.102-109.723
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European Journal of Chemistry 5(3), 383, 2014
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Polycyclic Aromatic Compounds , 1, 2023
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DOI Link: https://doi.org/10.5155/eurjchem.4.2.102-109.723
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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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