Synthesis of New Pyrazoline-Nucleoside Analogue Derivatives

In this work, a synthesis of pyrazoline nucleosides analogues is presented, using the stereospecific sodium salt glycosylation procedure. In the first step, chalcones were prepared using Claisen–Schmidt reaction by reacting benzaldehyde with enolizable ketones in ethanolic NaOH solutions. Next, thes...

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Bibliographic Details
Published in:	Nucleosides, nucleotides & nucleic acids Vol. 32; no. 6; pp. 294 - 305
Main Authors:	Azouz, M., Lammara, K., Benallia, M., Guenane, H.
Format:	Journal Article
Language:	English
Published:	United States Taylor & Francis Group 01-01-2013
Subjects:	aldol condensation Chemistry Techniques, Synthetic Glycosylation ketones enolization nucleosides Nucleosides - chemical synthesis Nucleosides - chemistry Pyrazoles - chemical synthesis Pyrazoles - chemistry α,α′-Bis(substituted benzylidene) cycloalkanones
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Summary:	In this work, a synthesis of pyrazoline nucleosides analogues is presented, using the stereospecific sodium salt glycosylation procedure. In the first step, chalcones were prepared using Claisen–Schmidt reaction by reacting benzaldehyde with enolizable ketones in ethanolic NaOH solutions. Next, these chalcones were immediately reacted with hydrazine hydrochloride in the presence of dry methanol to obtain the corresponding 2-pyrazolines. Finally, the coupling of the pyrazolines with 1-chloro-arabinofuranose leads to different β-nucleosides as the major product (13–17) in good yields. The structures of these derivatives were characterized by infrared and 1HNMR spectroscopy and mass spectrometry.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1525-7770 1532-2335
DOI:	10.1080/15257770.2013.786834