Chemistry of N-functionalized spirodihydroquinolines. Unusual access to the 3-methyl-4-(2-oxo-pyrrolidinyl-1)spiro[indane-1,1′-cyclohexanes] from 1-(3-cyanopropyl)-3,4-dihydrospiro[quinoline-2,1′-cyclohexanes] |
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Authors: | Vladimir Kouznetsov Alirio PalmaWilson Rozo Elena StashenkoAli Bahsas Juan Amaro-Luis |
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Abstract: | The transformation of N-substituted 3,4-dihydrospiroquinoline-2,1′-cyclohexanes] 2 and 3 has been examined in strong acid media, at elevated temperature. It was demonstrated that the N-(γ-cyanopropyl) spirodihydroquinolines 2 in the presence of concentrated sulfuric acid or PPA underwent hydrolysis affording the γ-aminoacids 3. The spirodihydroquinoline ring rearrangement readily produces 4-(2-oxopyrrolidinyl-1)spiroindane-1,1′-cyclohexanes] 5 in good yields. The structures of all synthesized compounds were established by means of homonuclear and inverse-detected 2D NMR experiments. |
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Keywords: | intramolecular Friedel-Crafts alkylation aminospiroindanes spirodihydroquinolines |
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