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Volumn 36, Issue 8, 2007, Pages 1056-1057

1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2,2,2]octane bis(tetrafluoroborate) as novel and efficient reagent for the conjugate addition of indoles to α,β-unsaturated ketones

(5) Yadav, J S a Reddy, B V Subba a Raju, A a Ravindar, K a Baishya, Gakul a

a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34548303551 PISSN: 03667022 EISSN: None Source Type: Journal
DOI: 10.1246/cl.2007.1056 Document Type: Article

Times cited : (4)

References (31)

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- General procedure. A mixture of indole (1 mmol) and α,β- unsaturated ketone (1 mmol) and Selectfluor™ (10 mol, in acetonitrile (10 mL) was stirred at room temperature for the appropriate time (Table 1, After completion of the reaction, as indicated by TLC, The solvent was evaporated under reduced pressure. Then, the resulting product was directly charged onto a small silica gel column and eluted with a mixture of ethyl acetate: n-hexane (1.5:8.5) to afford pure 3-substituted indoles. Spectral data for selected products: 3a. White solid, mp 94-95 °C; IR (KBr, v 3329, 3047, 2936, 2841, 1702, 1595, 1503, 1437, 1361, 1227, 1159, 1061, 934, 859, 746 cm -1; 1H NMR (200 MHz, CDCl3, δ 2.50 (s, 3H, 2.80 (t, 2H, J, 7.5 Hz, 3.04 (t, 2H, J, 7.5 Hz, 6.95 (d, 1H, J, 2.5 Hz, 7.00-7.18 (m, 2H, 7.22-7.32 (m, 1H, 7.50 (d, 1H, J, 7.0 Hz, 7.90 (brs, 1H, NH, 13C NMR 50 MHz, CDCl3, δ 20.1, 30.5
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