Synthesis of Phenanthridinones by Palladium-Catalyzed Cyclization of N-Aryl-2-aminopyridines with 2-Iodobenzoic Acids in Water

Xiaojuan Ding; Lei Zhang; Yiyang Mao; Binsen Rong; Ning Zhu; Jindian Duan; Kai Guo

doi:10.1055/s-0039-1691538

Synlett, Inhaltsverzeichnis

Synlett 2020; 31(03): 280-284
DOI: 10.1055/s-0039-1691538

letter

Synthesis of Phenanthridinones by Palladium-Catalyzed Cyclization of N-Aryl-2-aminopyridines with 2-Iodobenzoic Acids in Water

Xiaojuan Ding

^aCollege of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China eMail: duanjd@njtech.edu.cn eMail: guok@njtech.edu.cn

,

Lei Zhang

^aCollege of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China eMail: duanjd@njtech.edu.cn eMail: guok@njtech.edu.cn

,

Yiyang Mao

^aCollege of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China eMail: duanjd@njtech.edu.cn eMail: guok@njtech.edu.cn

,

Binsen Rong

^aCollege of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China eMail: duanjd@njtech.edu.cn eMail: guok@njtech.edu.cn

,

Ning Zhu

^aCollege of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China eMail: duanjd@njtech.edu.cn eMail: guok@njtech.edu.cn

,

Jindian Duan∗

^aCollege of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China eMail: duanjd@njtech.edu.cn eMail: guok@njtech.edu.cn

,

Kai Guo ∗

^aCollege of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China eMail: duanjd@njtech.edu.cn eMail: guok@njtech.edu.cn

^bState Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China

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Abstract

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Abstract

The first Pd-catalyzed cyclization of N-aryl-2-aminopyridines with 2-iodobenzoic acids for the synthesis of phenanthridinones through C–H bond activation under very low catalyst loadings (down to 0.1 mol% Pd) in water is reported. This protocol features a broad substrate scope and provides easy efficient access to various phenanthridinones.

Key words

phenanthridinones - palladium catalysis - cyclization - arylaminopyridines - iodobenzoic acids

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References and Notes

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16 Phenanthridinones 3; General Procedure Pd(OAc)₂ (4.5 mg, 0.02 mmol) was dissolved in CH₂Cl₂ (1 mL) and 10 μL of the solution was added to a Schlenk tube equipped with a Teflon-coated magnetic stirrer bar. The solvent was then evaporated under high vacuum. The appropriate N-aryl-2-aminopyridine 1 (0.20 mmol), 2-iodobenzoic acid 2 (0.26 mmol), and Ag₂O (32 mg, 0.14 mmol) were added to the Schlenk tube. Water (1.0 mL) was added, the tube was placed in a preheated oil bath (120 °C), and the mixture was stirred for 3 h. When the reaction was complete, the reaction tube was allowed to cool to r.t. and EtOAc was added. The organic layer was separated, and the aqueous layer was washed with EtOAc. The filtrate was concentrated under reduced pressure, and the crude product was purified by flash column chromatography (silica gel). 5-Pyridin-2-ylphenanthridin-6(5H)-one (3a) White solid; yield: 50 mg (93%); mp 185–186 °C. ¹H NMR (400 MHz, CDCl₃): δ = 8.77 (d, J = 4.1 Hz, 1 H), 8.53 (d, J = 7.9 Hz, 1 H), 8.27–8.22 (m, 2 H), 7.97–7.93 (m, 1 H), 7.76–7.73 (m, 1 H), 7.57–7.53 (m, 1 H), 7.46–7.42 (m, 2 H), 7.28–7.21 (m, 2 H), 6.51 (d, J = 8.4 Hz, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 161.7, 151.9, 150.6, 139.3, 138.2, 134.2, 133.0, 129.1, 128.8, 128.1, 125.7, 124.8, 124.1, 123.1, 122.9, 121.9, 118.9, 116.4. HRMS (ESI-TOF): m/z [M + H]⁺ calcd for C₁₈H₁₃N₂O: 273.1028; found: 273.1036.
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