Moron et al. Chem. Commun 2012;48:9171–9173. A cascade reaction of azolopyrimidines. Synthesis of unusual indole and azaindole derivatives.

Chem. Commun. 2012, 48, 9171

A cascade reaction of azolopyrimidines. Synthesis of unusual indole and azaindole derivatives.

María Morón¹, Carolina Burgos¹, Julio Alvarez-Builla¹, Antonio Salgado², Marta E. G. Mosquera^3, a, Juan J Vaquero^1, a

1. Departamento de Química Orgánica, Universidad de Alcalá, 28871-Alcalá de Henares, Madrid, Spain. 2. Department of Medicinal Chemistry, Centro Nacional de Investigaciones Oncológicas (CNIO), Melchor Fernández Almagro 3, E-28029-Madrid, Spain. 3. Departamento de Química Inorgánica Universidad de Alcalá, 28871-Alcalá de Henares, Madrid, Spain.

a. juanjose.vaquero@uah.es

Abstract

The reaction of bromo substituted pyrido[3',2':4,5]pyrrolo-[1,2-c]pyrimidine and pyrimido[1,6-a]indole methyl carboxylates with primary amines is described. The expected amide formation occurs but it is followed by an unexpected cascade process involving attack of the amine to the pyrimidine ring, opening of the pyrimidine ring, loss of the bromine substituent and competitive cyclizations to afford unusual imidazolidene substituted indoles and azaindoles.

QuiBio

Moron et al. Chem. Commun 2012;48:9171–9173. A cascade reaction of azolopyrimidines. Synthesis of unusual indole and azaindole derivatives.

Biological Chemistry Group