TY - JOUR
T1 - Coinage Metal-Catalyzed Divergent Heterocyclizations of Underexplored N-Propargyl Hydrazides
AU - Diez-Iriepa, Daniel
AU - Toledano-Pinedo, Mireia
AU - Herrera-Hernández, Lorena
AU - Samadi, Abdelouahid
AU - Raouf, Yasir S.
AU - Rodríguez-Fernández, M. Mercedes
AU - Flores-Galán, Paula
AU - Yanai, Hikaru
AU - Alonso, José M.
AU - Marco-Contelles, José
AU - Almendros, Pedro
N1 - Publisher Copyright:
© 2025 The Authors. Published by American Chemical Society
PY - 2025/9/5
Y1 - 2025/9/5
N2 - 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.
AB - 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.
UR - https://www.scopus.com/pages/publications/105015407625
UR - https://www.scopus.com/pages/publications/105015407625#tab=citedBy
U2 - 10.1021/acs.orglett.5c03069
DO - 10.1021/acs.orglett.5c03069
M3 - Article
C2 - 40862779
AN - SCOPUS:105015407625
SN - 1523-7060
VL - 27
SP - 9753
EP - 9758
JO - Organic Letters
JF - Organic Letters
IS - 35
ER -