A Novel Palladium-Based Heterogeneous Catalyst for Tandem Annulation: A Strategy for Direct Synthesis of Acridones

H. Sebastián Steingruber; Pamela Mendioroz; M. Julia Castro; María A. Volpe; Darío C. Gerbino

doi:10.1055/s-0042-1751371

Synthesis, Table of Contents

Synthesis 2023; 55(04): 692-706
DOI: 10.1055/s-0042-1751371

paper

A Novel Palladium-Based Heterogeneous Catalyst for Tandem Annulation: A Strategy for Direct Synthesis of Acridones

Authors

H. Sebastián Steingruber

^aInstituto de Química del Sur, INQUISUR (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, 8000 Bahía Blanca, Argentina
Pamela Mendioroz

^aInstituto de Química del Sur, INQUISUR (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, 8000 Bahía Blanca, Argentina
M. Julia Castro

^aInstituto de Química del Sur, INQUISUR (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, 8000 Bahía Blanca, Argentina
María A. Volpe

^bPlanta Piloto de Ingeniería Química (PLAPIQUI-CONICET), Camino La Carrindanga Km 7, 8000 Bahía Blanca, Argentina
Darío C. Gerbino∗

^aInstituto de Química del Sur, INQUISUR (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, 8000 Bahía Blanca, Argentina

Abstract

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Dedicated to Professor Hans-Günther Schmalz on the occasion of his 65^th 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 methodology

Full Text

References

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Supplementary Material

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