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Direct Conversion of 3-(2-Nitroethyl)-1H-Indoles into 2-(1H-Indol-2-yl)Acetonitriles |
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| Authors: | Alexander V Aksenov Nicolai A Aksenov Elena V Aleksandrova Dmitrii A Aksenov Igor Yu Grishin Elena A Sorokina Allison Wenger Michael Rubin |
| Institution: | 1.Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355017 Stavropol, Russia; (N.A.A.); (E.V.A.); (D.A.A.); (I.Y.G.);2.Organic Chemistry Department, Peoples’ Friendship University of Russia (RUDN University), 6, Miklukho-Maklaya St., 117198 Moscow, Russia;3.Department of Chemistry, University of Kansas, 1567 Irving Hill Road, Lawrence, KS 66045, USA; |
| Abstract: | The recently discovered 4+1]-spirocyclization of nitroalkenes to indoles provided a convenient new approach to 2-(1H-indol-2-yl)acetonitriles. However, this reaction was complicated by the formation of inert 3-(2-nitroethyl)-1H-indole byproducts. Herein, we offer a workaround this problem that allows for effective transformation of the unwanted byproducts into acetonitrile target molecules. |
| Keywords: | nitroalkanes heterocycles 1 2-alkyl shift rearrangements cascade transformations |