Domino Construction of Benzoxazole-Derived Sulfonamides <i>via</i> Metal-Free Denitrogenation of 5-Iodo-1,2,3-triazoles in the Presence of SO<sub>2</sub> and Amines
Avetik G. Gevondian, Yury N. Kotovshchikov, Gennadij V. Latyshev, Nikolay V. Lukashev, I. P. Beletskaya
Abstract
A straightforward domino approach to assemble benzoxazole-derived sulfonamides has been developed. The method is based on annulation-induced in situ generation of diazo compounds from readily available 2-(5-iodo-1,2,3-triazolyl)phenols, followed by metal-free denitrogenative transformation upon the action of 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO) and amines. The protocol is operationally simple and features a broad substrate scope, furnishing a library of target compounds in generally good yields.
Topics & Concepts
ChemistryBenzoxazoleDominoDiazoAnnulationOctaneCombinatorial chemistryPhenolsOrganic chemistryCatalysisCyclopropane Reaction MechanismsSulfur-Based Synthesis TechniquesClick Chemistry and Applications