Jump to main content
Jump to site search

Issue 19, 2014
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


Submitted
23 Dec 2013
Accepted
28 Jan 2014
First published
28 Jan 2014

RSC Adv., 2014,4, 9856-9865
Article type
Paper
Author version available

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

Social activity

Search articles by author

Spotlight

Advertisements