Coinage Metal-Catalyzed Divergent Heterocyclizations of Underexplored N-Propargyl Hydrazides

Daniel Diez-Iriepa; Mireia Toledano-Pinedo; Lorena Herrera-Hernández; Abdelouahid Samadi; Yasir S. Raouf; M. Mercedes Rodríguez-Fernández; Paula Flores-Galán; Hikaru Yanai; José M. Alonso; José Marco-Contelles; Pedro Almendros

doi:10.1021/acs.orglett.5c03069

Coinage Metal-Catalyzed Divergent Heterocyclizations of Underexplored N-Propargyl Hydrazides

Daniel Diez-Iriepa
, Mireia Toledano-Pinedo
, Lorena Herrera-Hernández
, Abdelouahid Samadi
, Yasir S. Raouf
, M. Mercedes Rodríguez-Fernández
, Paula Flores-Galán
, Hikaru Yanai
, José M. Alonso
, José Marco-Contelles
, Pedro Almendros

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	9753-9758
Number of pages	6
Journal	Organic Letters
Volume	27
Issue number	35
DOIs	https://doi.org/10.1021/acs.orglett.5c03069
Publication status	Published - Sept 5 2025

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.5c03069

Cite this

Diez-Iriepa, D., Toledano-Pinedo, M., Herrera-Hernández, L., Samadi, A., Raouf, Y. S., Rodríguez-Fernández, M. M., Flores-Galán, P., Yanai, H., Alonso, J. M., Marco-Contelles, J., & Almendros, P. (2025). Coinage Metal-Catalyzed Divergent Heterocyclizations of Underexplored N-Propargyl Hydrazides. Organic Letters, 27(35), 9753-9758. https://doi.org/10.1021/acs.orglett.5c03069

Diez-Iriepa, D, Toledano-Pinedo, M, Herrera-Hernández, L, Samadi, A , Raouf, YS, Rodríguez-Fernández, MM, Flores-Galán, P, Yanai, H, Alonso, JM, Marco-Contelles, J & Almendros, P 2025, 'Coinage Metal-Catalyzed Divergent Heterocyclizations of Underexplored N-Propargyl Hydrazides', Organic Letters, vol. 27, no. 35, pp. 9753-9758. https://doi.org/10.1021/acs.orglett.5c03069

@article{a8df5847b9954693ae4eba3d847e86a8,

title = "Coinage Metal-Catalyzed Divergent Heterocyclizations of Underexplored N-Propargyl Hydrazides",

abstract = "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.",

author = "Daniel Diez-Iriepa and Mireia Toledano-Pinedo and Lorena Herrera-Hern{\'a}ndez and Abdelouahid Samadi and Raouf, \{Yasir S.\} and Rodr{\'i}guez-Fern{\'a}ndez, \{M. Mercedes\} and Paula Flores-Gal{\'a}n and Hikaru Yanai and Alonso, \{Jos{\'e} M.\} and Jos{\'e} Marco-Contelles and Pedro Almendros",

note = "Publisher Copyright: {\textcopyright} 2025 The Authors. Published by American Chemical Society",

year = "2025",

month = sep,

day = "5",

doi = "10.1021/acs.orglett.5c03069",

language = "English",

volume = "27",

pages = "9753--9758",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "35",

}

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

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 -

Coinage Metal-Catalyzed Divergent Heterocyclizations of Underexplored N-Propargyl Hydrazides

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this