Enantioselective synthesis of bio-relevant 3,5-diaryl pyrazolines

The straightforward asymmetric construction of bio-relevant Δ(2)-pyrazolines having either N-(thio)amide or N-acetyl functional groups and flanked by aryl substituents such as phenol at C3 and C5 has been achieved through an enantioselective phase transfer organocatalytic addition of N-Boc hydrazine...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2012-05, Vol.10 (19), p.3946-3954
Main Authors: Mahé, Olivier, Dez, Isabelle, Levacher, Vincent, Brière, Jean-François
Format: Article
Language:English
Subjects:
Amides - chemistry
Chemical Sciences
Molecular Structure
Monoamine Oxidase Inhibitors - chemical synthesis
Monoamine Oxidase Inhibitors - pharmacology
Organic chemistry
Pyrazoles - chemical synthesis
Pyrazoles - pharmacology
Stereoisomerism
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Summary:The straightforward asymmetric construction of bio-relevant Δ(2)-pyrazolines having either N-(thio)amide or N-acetyl functional groups and flanked by aryl substituents such as phenol at C3 and C5 has been achieved through an enantioselective phase transfer organocatalytic addition of N-Boc hydrazine to chalcones followed by a transprotection sequence allowing N-Boc transformation into N-CXNHR (X = S, O) or N-Ac functional groups. This approach was applied to a straightforward elaboration of chiral monoamine oxidase inhibitor derivatives.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob25227a