Issue 13, 2013
From the journal:

RSC Advances

Capture of benzotriazole-based Mannich electrophiles by CH-acidic compounds†

Jean-Christophe M. Monbaliu,ab   Lucas K. Beagle,a   Finn K. Hansen,ac   Christian V. Stevens,b   Ciaran McArdled  and  Alan R. Katritzky*ae  

* Corresponding authors

a Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
E-mail: katritzky@chem.ufl.edu

b Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, B-9000 Ghent, Belgium

c Institut für Pharmazeutische and Medizinische Chemie, Heinrich Heine Universität Düsseldorf, Universitätsstr. 1, 40225 Düsseldorf, Germany

d Henkel Ireland Ltd., Tallaght Business Park, Whitestown Industrial Estate, Tallaght, Dublin 24, Ireland

e Chemistry Department, King Abdulaziz University, Jeddah, 21589 Saudi Arabia

Abstract

The Mannich-type capture reaction of aminoalkylbenzotriazoles by CH acidic compounds is documented. The pKa of the benzotriazole counteranion is key to the success of such reactions, whereas the global electrophilicity of the reactive iminium moiety is secondary.

Graphical abstract: Capture of benzotriazole-based Mannich electrophiles by CH-acidic compounds

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Article information

DOI
https://doi.org/10.1039/C3RA22826F
Article type
Communication
Submitted
08 Nov 2012
Accepted
14 Jan 2013
First published
16 Jan 2013

RSC Adv., 2013,3, 4152-4155

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Capture of benzotriazole-based Mannich electrophiles by CH-acidic compounds

J. M. Monbaliu, L. K. Beagle, F. K. Hansen, C. V. Stevens, C. McArdle and A. R. Katritzky, RSC Adv., 2013, 3, 4152 DOI: 10.1039/C3RA22826F

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