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Issue 19, 2014
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Synthesis of interesting β-nitrohydrazides through a thiourea organocatalysed aza-Michael addition

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Abstract

The synthesis of antimicrobial β-nitrohydrazides, as the target product of our reaction, is reached for the first time under organocatalytic enantioselective conditions. We accomplish this goal by using a thiourea organocatalysed aza-Michael addition reaction of hydrazide to nitroalkenes, furnishing final products with good yields and good enantiomeric ratios. The developed methodology is one of the rare examples of catalytic reactivity using hydrazide where the reaction proceeds through its N2 atom. Our developed strategy extends the generality of this area of research due to the difficulties of designing new nitrogen nucleophiles with high activity, and in addition, this is one of the scarce examples where nitroalkenes and chiral thioureas have been used in asymmetric organocatalytic aza-Michael addition reactions.

Graphical abstract: Synthesis of interesting β-nitrohydrazides through a thiourea organocatalysed aza-Michael addition

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Publication details

The article was received on 23 Dec 2013, accepted on 28 Jan 2014 and first published on 28 Jan 2014


Article type: Paper
DOI: 10.1039/C3RA47925K
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RSC Adv., 2014,4, 9856-9865

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    Synthesis of interesting β-nitrohydrazides through a thiourea organocatalysed aza-Michael addition

    A. Alcaine, E. Marqués-López and R. P. Herrera, RSC Adv., 2014, 4, 9856
    DOI: 10.1039/C3RA47925K

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