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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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 CH2 Cl2 (3 × 15
mL). The combined organic extract was washed with brine and dried over
(Na2 SO4 ). 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 . ¹ H
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, C3 H 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, C4 H of quinolone and ArH). ¹³ C
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 C14 H12 N2 O [M + H]:
225.1016; found: 225.1022.
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