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Synlett 2019; 30(01): 63-68
DOI: 10.1055/s-0037-1610333
DOI: 10.1055/s-0037-1610333
letter
One-Pot Approach to Pyrido-4-phenanthridinones by Palladium-Catalyzed Annulation of 4-Quinolones with 2-Bromobenzyl Bromides
Further Information
Publication History
Received: 18 October 2018
Accepted after revision: 29 October 2018
Publication Date:
28 November 2018 (online)
Abstract
A straightforward approach toward the assembly of phenanthridinone heterocycles has been developed through the palladium-catalyzed N-benzylation/intramolecular coupling reactions of readily prepared 4-quinolones with commercially available 2-bromobenzyl bromide derivatives. The target products were prepared in moderate to good yields, with tolerance of various functional groups.
Key words
one-pot reaction - palladium catalysis - quinolones - phenanthridinones - polycyclic heterocycles - bromobenzyl bromidesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610333.
- Supporting Information
- CIF File
-
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- 18 Phenanthridinone Derivatives 7 and 9; General Procedure A mixture of the appropriate quinolone 1 (1 mmol), 2-bromobenzyl bromide 5 or 8 (1.5 mmol), and K2CO3 (2 mmol) in anhyd DMF (3 mL) was stirred at 80 °C for 2 h, then cooled to r.t. TBAB (1.5 equiv), K2CO3 (1.5 equiv), and Pd(OAc)2 (10 mol %) were added to the reaction vessel under argon, and the mixture was heated at 80 °C for 3 h. When the reaction was complete, the mixture was cooled and diluted with H2O then extracted with EtOAc. The combined organic extracts were washed with H2O and brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography [silica gel, CHCl3–MeOH (9:1)]. Ethyl 2-Fluoro-4-oxo-4H,8H-pyrido[3,2,1-de]phenanthridine-5-carboxylate (7b) Light-yellow solid; yield: 0.116 g (85%); mp 230–232 °C. IR (KBr): 3423, 2924, 1721, 1603 cm–1. 1H NMR (400 MHz, DMSO-d6 ): δ = 8.67 (s, 1 H, ArH), 8.34 (dd, J = 3.2, 6.4 Hz, 1 H, ArH), 8.15–8.13 (m, 1 H, ArH), 7.78 (dd, J = 3.2, 5.6 Hz, 1 H, ArH), 7.49–7.46 (m, 2 H, ArH), 7.36 (t, J = 4.8 Hz, 1 H, ArH), 5.56 (s, 2 H, N–CH2), 4.26 (q, J = 6.8 Hz, 2 H, CH2), 1.30 (t, J = 6.4 Hz, 3 H, CH3). 13C APT (100 MHz, DMSO-d6 ): δ = 172.8, 165.2, 161.1, 158.7, 150.9, 136.3, 134.8, 133.6, 130.5, 130.3, 128.8, 128.2, 122.1, 121.7, 121.4, 120.9, 120.8, 111.6, 111.4, 110.4, 60.2, 56.8, 14.7. HRMS (TOF-ES+): m/z [M + H]+ calcd for C19H15FNO3: 324.1 found: 324.0253.
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