Design and synthesis of two triazonine-carbaldehyde derivatives using several chemical tools

• Published in: Journal of Saudi Chemical Society Vol. 22; no. 2; pp. 183 - 197
• Main Authors: Figueroa-Valverde, Lauro, Díaz-Cedillo, Francisco, García-Cervera, Elodia, Pool-Gómez, Eduardo, Rosas-Nexticapa, Marcela, López-Ramos, María, Vera-Escobedo, Maria Isabel
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01-02-2018; Elsevier
• Subjects: Boric acid; p-Nitrobenzoyl azide; Testosterone; Triazonine; Testosterone; Boric acid; p-Nitrobenzoyl azide; Triazonine
• ISSN: 1319-6103
• DOI: 10.1016/j.jscs.2016.03.003

Several triazonine-carbaldehyde derivatives have been prepared using different protocols; however, some require special reagents and conditions. The aim of study involved the synthesis of two triazonine-carbaldehyde derivative using testosterone or OTBS-testosterone as chemical tool. Triazonine-carbaldehyde derivatives were prepared by a series of reactions that involve the following: (1) synthesis of two nitrobenzamide derivatives by reaction of testosterone or OTBS-testosterone with p-nitrobenzoyl azide using Copper(II) as catalyst; (2) reaction of the nitrobenzamides with ethylenediamine to form two triazonine derivatives using boric acid as catalyst; (3) preparation of hexynyl-triazonine derivatives by the reaction of two triazonines 6-chlorohex-1-yne in basic medium; (4) reaction of hexynyl-triazonine derivatives with benzaldehyde to form two triazoninol analogs; (5) preparation of triazoninynal derivatives through oxidation of triazoninol analogs with dimethyl sulfoxide; and (6) synthesis of triazonine-carbaldehyde derivatives by the reaction of triazoninynal derivatives with hexyne-1 using Copper(II) as catalyst. The chemical structure of compounds was determined by spectroscopic and spectrometric methods. In conclusion, in this work were prepared two triazoninone derivatives using several chemical techniques, which are simple procedures and easy to handle.