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Typical Procedure
for the Synthesis of Pyrano[2,3-
b
]quinolines (2a as an example)
The
substrate 1a (217 mg, 1.0 mmol) and CF3SO3H
(0.35 mL, 4.0 mmol) was well stirred at 80 ˚C for 6.0 h.
When the substrate 1a had been consumed
(monitored by TLC), the mixture was poured into sat. aq NaCl (50
mL), neutralized with sat. aq NaHCO3, and extracted with
CH2Cl2 (3 × 20 mL).
The combined organic phase was washed with H2O (3 × 20
mL), dried over MgSO4, filtered, and concentrated in vacuo.
The crude product was purified by flash chroma-tography (silica
gel, PE-Et2O = 2:1) to give 2a as a white solid (173 mg, 87%).
Selected Data for Compound 2a
White
solid; mp 158-161 ˚C. ¹H
NMR (400 MHz, CDCl3): δ = 2.09-2.15
(m, 2 H), 2.55 (s, 3 H), 2.93 (t, J = 6.8
Hz, 2 H), 4.40 (t, J = 5.2
Hz, 2 H), 7.37 (t, J = 8.0
Hz, 1 H), 7.57 (t, J = 8.0
Hz, 1 H), 7.81 (d, J = 8.4
Hz 1 H), 7.87 (d, J = 8.4 Hz,
1 H). ¹³C NMR (100 MHz, CDCl3): δ = 13.3,
21.8, 23.4, 66.5, 116.4, 123.5, 125.0, 127.6, 128.5, 144.0, 145.3,
159.4. IR (KBr): 2945, 1591, 1502, 1408, 1317, 1246, 1178, 1124, 980,
756 cm-¹. Anal. Calcd for C13H13NO:
C, 78.36; H, 6.58; N, 7.03. Found: C, 78.12; H, 6.33; N, 7.31.
15 For the analytical data of 2, see Supporting Information.
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