<i>N</i>-Iodosuccinimide-Promoted [3 + 2] Annulation Reaction of Aryldiazonium Salts with Guanidines To Construct Aminotetrazoles
Yilin Yang, Shen Li, Fa‐Guang Zhang, Jun‐An Ma
Abstract
A N-iodosuccinimide (NIS)-promoted [3 + 2] annulation reaction of aryldiazonium salts with guanidines has been developed for the construction of previously elusive 2-aryl-5-amino-2H-tetrazoles. This transformation takes advantage of readily available starting materials, proceeds under metal-free, mild, and robust conditions, and holds broad functional group compatibility. The utility of this protocol is further manifested via coupling, annulation, deamination, and denitrogenation derivatizations.
Topics & Concepts
ChemistryAnnulationDeaminationCombinatorial chemistryArylReaction conditionsFunctional groupOrganic chemistryCatalysisAlkylEnzymePolymerSynthesis of Tetrazole DerivativesQuinazolinone synthesis and applicationsMulticomponent Synthesis of Heterocycles