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An Efficient Approach to 2-CF3-Indoles Based on ortho-Nitrobenzaldehydes |
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| Authors: | Vasiliy M Muzalevskiy Zoia A Sizova Vladimir T Abaev Valentine G Nenajdenko |
| Institution: | 1.Department of Chemistry, Lomonosov Moscow State University, 119899 Moscow, Russia; (V.M.M.); (Z.A.S.);2.North Ossetian State University, 44-46 Vatutina St., 362025 Vladikavkaz, Russia;3.North Caucasus Federal University, 1a Pushkin St., 355009 Stavropol, Russia |
| Abstract: | The catalytic olefination reaction of 2-nitrobenzaldehydes with CF3CCl3 afforded stereoselectively trifluoromethylated ortho-nitrostyrenes in up to 88% yield. The reaction of these alkenes with pyrrolidine permits preparation of α-CF3-β-(2-nitroaryl) enamines. Subsequent one pot reduction of nitro-group by Fe-AcOH-H2O system initiated intramolecular cyclization to afford 2-CF3-indoles. Target products can be prepared in up to 85% yields. Broad synthetic scope of the reaction was shown as well as some followed up transformations of 2- CF3-indole. |
| Keywords: | CF3-group catalytic olefination reaction nitro group reduction indole fluorine |