Annulation-Induced Cascade Transformation of 5-Iodo-1,2,3-triazoles to 2-(1-Aminoalkyl)benzoxazoles

Abstract

Base-mediated cyclization of (5-iodo-1,2,3-triazolyl)phenols was proposed as a new synthetic strategy for the in situ generation of diazoimines via electrocyclic ring opening of the fused heterocycle. Cu-catalyzed amination of the intermediate diazoalkanes was employed to develop an efficient cascade approach to functionalized benzoxazoles.

Oxo-functionalised mesoionic NHC nickel complexes for selective electrocatalytic reduction of CO2 to formate

“…General 2-Azidophenol 1, 1-(2-phenol)-imidazole 7 and 2-amino-4,6-ditertbutylphenol were synthesized following procedures reported in literature. [61][62][63] The synthesis of all triazolium salt ligand precursors (2a-c, 5a-b) is detailed in the ESI. † All other reagents were commercially available and used as received.…”

Regioselective Synthesis of Halotriazoles and their Utility in Metal Catalyzed Coupling Reactions

“…The existence of diazo tautomer 194 was confirmed by presence of strong band at 2065 cm –1 in the IR spectrum. [ 69 ]…”

5-Iodo-1H-1,2,3-triazoles as Versatile Building Blocks

“…Base-mediated cyclization of 2-(5-iodotriazol-1-yl)phenols 159 was proposed as a new synthetic strategy for the in situ generation of diazoimines B via electrocyclic ring opening of the initially formed benzoxazolotriazoles A (Scheme 44). 140 The subsequent Bamford-Stevens-type denitrogenation afforded alkenes. The possibility of trapping diazoimines B with amines was also studied.…”