One-Pot Synthesis of Pyrano[2,3-b]quinolines from Enaminones
under Solvent-Free Conditions

Dexuan Xiang; Xiaoqing Xin; Xu Liu; Santosh Kumar; Dewen Dong

doi:10.1055/s-0030-1261198

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Synlett 2011(15): 2187-2190
DOI: 10.1055/s-0030-1261198

LETTER

One-Pot Synthesis of Pyrano[2,3-b]quinolines from Enaminones under Solvent-Free Conditions

Dexuan Xiang, Xiaoqing Xin, Xu Liu, Santosh Kumar, Dewen Dong*
Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. of China
e-Mail: dwdong@ciac.jl.cn;

Further Information

Publication History

Received 15 May 2011
Publication Date:
30 August 2011 (online)

Abstract
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References
Supplementary Material

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Abstract

A facile and efficient one-pot synthesis of pyrano[2,3-b]quinolines has been developed via the Combes-type reaction of readily available enaminones, 2-arylamino-3-acetyl-5,6-dihydro-4H-pyrans, mediated by trifluoromethanesulfonic acid under solvent-free conditions.

Key words

pyranoquinolines - Combes-type reaction - enaminones - trifluoromethanesulfonic acid - solvent-free

Supporting Information

References and Notes

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14

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.

Supplementary Material

Supporting Information