Regioselective Synthesis of Annulated Quinoline and Pyridine Derivatives by Silver-Catalyzed 6-endo-dig Cycloisomerization

Abstract

3H-pyrano[3,2-f]quinoline-3-one, 4-methyl-4,7-phen­anthrolin-3(4H)-one, and 1,3-dimethylpyrido[3,2-d]pyrimidine-2,4(1H,3H)-dione derivatives have been synthesized by hitherto unreported silver-catalyzed 6-endo-dig mode of cycloisomerization from various N-propargylated heterocyclic compounds. The silver-catalyzed reaction provides the synthesis of potential bioactive compounds in excellent yields.

Key words

3H-pyrano[3,2-f]quinoline-3-one - 4-methyl-4,7-phen­anthrolin-3(4H)-one - 1,3-dimethylpyrido[3,2-d]pyrimidine-2,4(1H,3H)-dione - AgSbF₆ - cycloisomerization - 6-endo-dig

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19

Synthesis of 4,10-Dimethyl-4,7-phenanthrolin-3 (4 H )-one (4d) To a stirred solution of AgSbF₆ (7.6 mg, 0.022 mmol) in DMSO (5 mL), 6-(but-2-ynylamino)-1-methylquinolin-2 (1H)-one (3d, 50 mg, 0.22 mmol) was added at r.t. and stirred at 110 ˚C for 45 min to complete the reaction (as monitored by TLC). The light green colored reaction mixture was cooled and neutralized with sat. NaHCO₃ solution. This was extracted with CH₂Cl₂ (3 × 15 mL). The combined organic extract was washed with brine and dried over (Na₂SO₄). The solvent was distilled off. The resulting crude product was purified by column chromatography over silica gel (60-120 mesh) using PE-EtOAc mixture (3:2) as an eluent to give the product 4d. Yield 96%, yellow solid, mp 172 ˚C. IR (KBr): 1646, 1561 cm^-¹. ^¹H NMR (400 MHz, CDCl₃): δ = 3.00 (s, 3 H, CH₃), 3.88 (s, 3 H, NCH₃), 6.81 (d, 1 H, J = 10.0 Hz, C₃H of quinolone), 7.34 (d, 1 H, J = 4.4 Hz, ArH), 7.77 (d, 1 H, J = 9.6 Hz, ArH), 8.22 (d, 1 H, J = 9.2 Hz, ArH), 8.72 (d, 2 H, J = 10.0 Hz, C₄H of quinolone and ArH). ^¹³C NMR (100 MHz, CDCl₃): δ = 26.4, 30.6, 115.6, 117.9, 119.7, 125.8, 126.5, 134.2, 136.9, 140.4, 143.3, 145.4, 148.6, 161.5. HRMS: m/z calcd for C₁₄H₁₂N₂O [M + H]: 225.1016; found: 225.1022.