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Synlett 2016; 27(03): 387-390
DOI: 10.1055/s-0035-1560962
DOI: 10.1055/s-0035-1560962
letter
Catalyst-Free Friedel–Crafts Alkylation of Imidazo[1,2-α]pyridines
Further Information
Publication History
Received: 23 August 2015
Accepted after revision: 16 October 2015
Publication Date:
20 November 2015 (online)
Abstract
A catalyst-free Friedel–Crafts alkylation of imidazo[1,2-α]pyridines with β-nitrostyrenes was developed. Electron-donating and electron-withdrawing functional groups at various aromatic positions were well tolerated under our optimized conditions. This method provides an efficient and environmentally benign route to synthesize imidazo[1,2-α]pyridine-nitroalkane derivatives in moderate to excellent yields.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560962.
- Supporting Information
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References and Notes
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- 12 Catalyst-Free F–C Alkylation of Imidazo[1,2-α]pyridines with β-Nitrostyrene in tert-Butanol; General Procedure: To a stirred solution of the imidazo[1,2-α]pyridine (0.10 mmol) in t-BuOH (1.0 mL), the β-nitrostyrene (0.20 mmol) was added under argon atmosphere. The mixture was stirred at 80 °C for 24 h. Then the solvent was removed in vacuo, and the residue was purified by preparative thin-layer chromatography (PE–EtOAc, 3:2) to give the product. 3-(2-Nitro-1-phenylethyl)-2-phenylimidazo[1,2-α]pyridine (3aa): brown solid; mp 90–91 °C. 1H NMR (600 MHz, CDCl3): δ = 7.72 (d, J = 6.6 Hz, 1 H), 7.67 (d, J = 9.0 Hz, 1 H), 7.62 (d, J = 6.6 Hz, 2 H), 7.41–7.46 (m, 3 H), 7.30–7.37 (m, 3 H), 7.20–7.27 (m, 3 H), 6.74 (t, J = 6.6 Hz, 1 H), 5.62 (t, J = 7.8 Hz, 1 H), 5.08 (dd, J = 13.2, 7.8 Hz, 1 H), 4.96 (dd, J = 13.2, 7.8 Hz, 1 H). 13C NMR (150 MHz, CDCl3): δ = 145.5, 145.2, 136.1, 134.4, 129.6, 129.2, 128.6, 128.5, 128.2, 126.9, 124.8, 123.3, 118.1, 116.7, 112.8, 76.6, 39.3. HRMS (+ve, ESI): m/z [M + H]+ calcd for C21H18N3O2 +: 344.1394; found: 344.1397.
For selected examples, see:
For selected examples, see: