Organochalcogen compounds (with C-E bonds; E = S, Se and Te) have been widely studied due to the large number of synthetic and biological applications. On the other hand, the benzotriazolic nucleus constitutes a variety of compounds that also have relevant biological properties. Thus, the combination of both in the same molecule, could be a powerful alternative to achieve a promising class for treatment of various diseases.1 In this context, the chalcogenfunctionalization of alkenes, using benzotriazole as a nitrogen source, offers an excellent perspective in organic synthesis, since the products are versatile and, still, little investigated. Therefore, in this work, the objective is the regioselective aminochalcogenation of alkenes, using benzotriazole as a nitrogen source, through an environmentally appropriate methodology.
The best condition found, under microwave irradiation (MW), was 20 mol% of iodine, 2 equivalents of DMSO at 65 °C and 100 W. The desire product was obtained in 89% yield. After determining the optimized conditions, the scope and limitations of the proposed methodology were investigated. Thus, a variety of β-amino selenides, sulfides and tellurides was developed, with yields ranging from 16-89% and which can be considered a promising alternative in the development of new drugs (Scheme 1).
After successful reactions, twenty-one compounds were sent for evaluation of potential biological activity against the new coronavirus, SARS-CoV-2, and six of them presented positive results.
In conclusion, we have developed a fast and sustainable approach to the aminochalcogenation of alkenes, using an oxidative catalytic system composed of I2/DMSO.