Synthesis of 9-alkyl-6-amino[1,2,4]triazolo[3,4-c]-5-azaquinoxalines. Mild and effective SNAr amination of highly electron-poor heterocycles |
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| Authors: | Asier Unciti-Broceta María José Pineda-de-las-Infantas Antonio Espinosa |
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| Institution: | a School of Chemistry, University of Edinburgh, West Mains Road, Edinburgh EH9 3JJ, UK
b Departamento de Química Farmacéutica y Orgánica, Facultad de Farmacia, Universidad de Granada, Campus Cartuja s/n, 18071 Granada, Spain |
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| Abstract: | The synthesis and characterization of five different 9-alkyl-6-amino1,2,3]triazolo3,4-c]-5-azaquinoxalines is described. Due to the notable electrophilic character of the C-6 position of the 1,2,4]triazolo3,4-c]-5-azaquinoxaline tricyclic system, SNAr amination was achieved simply by reacting the corresponding 6-chloro derivative with ammonia-saturated acetonitrile (a non-nucleophilic polar solvent) in a sealed reaction vessel, using microwave-mediated or conventional heating. |
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