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Synthesis 2023; 55(04): 692-706
DOI: 10.1055/s-0042-1751371
DOI: 10.1055/s-0042-1751371
paper
A Novel Palladium-Based Heterogeneous Catalyst for Tandem Annulation: A Strategy for Direct Synthesis of Acridones
This work was generously supported by the National Council of Scientific and Technical Research (Consejo Nacional de Investigaciones Científicas y Técnicas; CONICET), the National Agency for Scientific and Technological Promotion (Agencia Nacional de Promoción Científica y Tecnológica; ANPCyT), and the Universidad Nacional del Sur (Secretaría General de Ciencia y Tecnología, Universidad Nacional del Sur; SGCyT-UNS), Argentina.
Dedicated to Professor Hans-Günther Schmalz on the occasion of his 65th birthday
Abstract
In order to develop an efficient, rapid, and modular cascade strategy for the direct synthesis of acridones, palladium supported on sulfated alumina and microwave activation are employed. Multifunctional heterogeneous palladium catalysts were prepared in order to carry out the sequential annulation via a Buchwald–Hartwig amination followed by an intramolecular annulation in a one-pot process. This new protocol represents the first report on a catalytic tandem synthesis of acridone derivatives from commercially available starting materials, under ligand-free conditions. The scope of the present methodology is extended to the generation of a library of functionalized acridones, showing high functional group compatibility, in moderate to excellent yields. The applicability of this novel transformation was demonstrated by the concise total synthesis of the natural product arborinine.
Key words
acridones - tandem reaction - palladium catalysis - sulfated alumina - synthetic methodologySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751371.
- Supporting Information
Publication History
Received: 29 July 2022
Accepted after revision: 12 September 2022
Article published online:
11 October 2022
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