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Access to fused indolines with a quaternary N,N′-aminal center

Year: 2026

Type: article

Abstract: A highly efficient one-pot sequence has been developed for the rapid construction of fused polycyclic indolines bearing a C2-N,N′-aminal quaternary center. The process, which employs 1,2-diaza-1,3-dienes and 2-substituted indoles as key substrates, proceeds through a Zn(II)-catalyzed Michael addition, followed by an intramolecular Cu(II)-catalyzed dearomative oxidative cyclization. This sequence enabling N–C(sp$^2$) bond formation via formal C(sp$^2$)–H activation, azoalkene addition, and aza-Wacker-type cyclization exhibits broad substrate tolerance and delivers unprecedented tricyclic indole architectures (namely 9a-substituted 9,9a-dihydro-1H-pyridazino[3,4-b]indoles) in good to excellent yields.

Source: Repository of the University of Ljubljana (University of Ljubljana)

Authors: Caselli, Sara, Golobič, Amalija, Mantellini, Fabio, Mari, Giacomo, Favi, Gianfranco

Institutions: University of Ljubljana, University of Urbino

Language: English

Topic: Synthesis of Indole Derivatives

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: European Commission, Univerza v Ljubljani, Università degli Studi di Urbino Carlo Bo

Awards: G1455722668, G579330274

OpenAlex ID: W7154545601

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