Issue 35, 2014
From the journal:

Chemical Communications

A gold-catalysed imine–propargylamine cascade sequence: synthesis of 3-substituted-2,5-dimethylpyrazines and the reaction mechanism†

Benito Alcaide,*a   Pedro Almendros,*b   José M. Alonso,a   Israel Fernández,c   Gonzalo Gómez-Campillosa  and  M. Rosario Torresd  

* Corresponding authors

a Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain
E-mail: alcaideb@quim.ucm.es
Fax: +34 91-3944103

b Instituto de Química Orgánica General, IQOG-CSIC, Juan de la Cierva 3, 28006-Madrid, Spain
E-mail: Palmendros@iqog.csic.es
Fax: +34 91-5644853

c Departamento de Química Orgánica, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain

d CAI Difracción de Rayos X, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain

Abstract

The gold-catalysed coupling reaction between propargylamine-derived imines and propargylamine exclusively afforded pyrazines. Besides, in order to understand the mechanism of this sequence, deuterium labeling and computational studies have been performed.

Graphical abstract: A gold-catalysed imine–propargylamine cascade sequence: synthesis of 3-substituted-2,5-dimethylpyrazines and the reaction mechanism

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Article information

DOI
https://doi.org/10.1039/C4CC01485E
Article type
Communication
Submitted
26 Feb 2014
Accepted
12 Mar 2014
First published
13 Mar 2014

Chem. Commun., 2014,50, 4567-4570

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A gold-catalysed imine–propargylamine cascade sequence: synthesis of 3-substituted-2,5-dimethylpyrazines and the reaction mechanism

B. Alcaide, P. Almendros, J. M. Alonso, I. Fernández, G. Gómez-Campillos and M. R. Torres, Chem. Commun., 2014, 50, 4567 DOI: 10.1039/C4CC01485E

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