Annulation-Triggered Denitrogenative Transformations of 2-(5-Iodo-1,2,3-triazolyl)benzoic Acids

The ability of [1,2,3]triazolobenzoxazinones to act as a source ofhiddendiazo group was discovered. These diazoprecursors can be easily prepared by the intramolecular cyclizationof 2-(5-iodo-1,2,3-triazolyl)benzoic acids. The Cu-catalyzedcapture of the hidden diazo group allows for further functionaliza-tion through the denitrogenative pathway. The transformationsproceedviathe formation of either diazoimine or diazoamideintermediates. Novel routes to various anthranilamides as well asthiolated benzoxazinones were developed using the one-potcyclization/diazo capture procedure.

Automated summary

The ability of [1,2,3]triazolobenzoxazinones to serve as a source of hidden diazo groups has been discovered. These diazo precursors can be easily prepared through intramolecular cyclization and further functionalized using Cu-catalyzed diazo capture. Various anthranilamides and thiolated benzoxazinones can be synthesized using this one-pot cyclization/diazo capture procedure.