European Journal of Chemistry

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



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Hamdi Mahmoud Hassaneen
Ahmad Sami Shawali

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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Hassaneen, H. M.; Shawali, A. S. Regioselective Synthesis of Some Functionalized 3,4’-Bis-(pyrazolyl)ketones and Chemoselectivity in Their Reaction With Hydrazine Hydrate. Eur. J. Chem. 2013, 4, 102-109.

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