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RESEARCH ARTICLE
Contents Vol 67(2)

On-Water Reactivity and Regioselectivity of Quinones in C–N Coupling with Amines: Experimental and Theoretical Study

Maximiliano Martínez-Cifuentes A C , Graciela Clavijo-Allancan A , Carolina Di Vaggio-Conejeros A , Boris Weiss-López B and Ramiro Araya-Maturana A C
+ Author Affiliations
- Author Affiliations

A Departamento de Química Orgánica y Fisicoquímica, Facultad de Ciencias Químicas Y Farmacéuticas, Universidad de Chile, Casilla 233, Santiago 1, Chile.

B Departamento de Química, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago, Chile.

C Corresponding authors. Email: mmartinez@ug.uchile.cl; raraya@ciq.uchile.cl

Australian Journal of Chemistry 67(2) 217-224 https://doi.org/10.1071/CH13355
Submitted: 6 July 2013  Accepted: 10 September 2013   Published: 11 October 2013

Abstract

A study about the oxidative coupling of some representative carbo- and heterocyclic non-symmetrical quinones with aryl- and alkylamines, was carried out comparing dichloromethane and water as reaction mediums. We found that the on-water reactions gave better or, at worst, the same results as a conventional organic medium like dichloromethane. Descriptors derived from conceptual density functional theory and approaches of electrostatic nature, such as the molecular electrostatic potential, were used to explain the observed chemical reactivity and regioselectivity. Further, the on-water conditions were used to obtain 24 new aminoquinones with potential biological activity.


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