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. 2023 Sep 1;88(17):12738-12743.
doi: 10.1021/acs.joc.3c01429. Epub 2023 Aug 23.

Construction of Phenanthridinone Skeletons through Palladium-Catalyzed Annulation

Xin Geng  1 , Heng He  1 , Andrey Shatskiy  2 , Elena V Stepanova  2   3 , Gregory R Alvey  2 , Jian-Quan Liu  1   2 , Markus D Kärkäs  2 , Xiang-Shan Wang  1
Affiliations

Construction of Phenanthridinone Skeletons through Palladium-Catalyzed Annulation

Xin Geng et al. J Org Chem. .

Abstract

Herein, a straightforward synthetic approach for the construction of phenanthridin-6(5H)-one skeletons is disclosed. The developed protocol relies on palladium catalysis, providing controlled access to a range of functionalized phenanthridin-6(5H)-ones in 59-88% yields. Furthermore, plausible reaction pathways are proposed based on mechanistic experiments.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Relevance and synthetic approaches to phenanthridin-6(5H)-one derivatives.
Scheme 1
Scheme 1. Reaction Scope and Synthetic Application,
Reaction conditions: Reactions were carried out with 1 (0.50 mmol), 2 (0.60 mmol), Pd(OAc)2 (12 mg, 0.05 mmol), PPh3 (26 mg, 0.10 mmol), and Cs2CO3 (326 mg, 1.0 mmol) in DMF (5.0 mL) under argon at 120 °C for 10 h. Isolated product yields are reported. Reaction carried out on a 1 mmol scale.
Scheme 2
Scheme 2. Investigations for Probing the Reaction Mechanism and Proposed Reaction Mechanism,
Reaction conditions: Reactions were carried out with 1 (0.50 mmol), 2 (0.60 mmol), Pd(OAc)2 (12 mg, 0.05 mmol), PPh3 (26 mg, 0.10 mmol), and Cs2CO3 (326 mg, 1.0 mmol) in DMF (5.0 mL) under argon at 120 °C for 10 h. Isolated product yields are reported. Regioisomeric ratios were determined by 1H NMR analysis.
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