Uso de ultrassom na síntese de 1,2,3-triazóis contendo selênio via cicloadição [3+2] enamino-azida

Abstract

In this work, we describe the use of sonochemistry as an alternative source of energy for the synthesis of triazoles containing an organic portion of selenium in their structure through [3+2] enamino-azide cycloaddition reactions. Reactions were performed between arilselanyl phenylazides 1 and 1,3- dicarbonyl 2 using 1 mol% diethylamine as organocatalyst, DMSO as solvent under ultrasound irradiation at 40% of amplitude. A series of triazoles 3 were obtained in good yields in reaction times of 5 minutes. This methodology proved to be efficient for a variety of substrates, providing the arilselanyl-1H-1,2,3-triazoles in good yields ranging from 56 to 93% (3a-p). It was possible to observe the effectiveness of the method used for the respective reaction, since a series of compounds were obtained with satisfactory yields and it was possible to extend the method to reactions with β- keto esters, β-keto amides and α-cyano ketones.