Metal-catalyzed reactions generate diazacyclic frameworks in N-propargyl hydrazides, highlighting both gold and silver's roles.
Herein, we disclose metal-catalyzed tunable annulations of uncharted alkyne-tethered hydrazides for the divergent preparation of diazacyclic frameworks. Cationic gold facilitates the O-cyclization, providing valuable [1,3,4]oxadiazine scaffolds with total selectivity, whereas silver catalysis promotes controlled N-cyclization to access N-acyl pyrazoles. Furthermore, density-functional-theory-based theoretical investigations support two different pathways (ionic versus radical) operating in the catalytic heterocyclization reaction of the same N-propargyl hydrazide substrate.
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Diez‐Iriepa et al. (2025) studied this question.
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