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The transformation of N-substituted 3,4-dihydrospiro[quinoline-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)spiro[indane-1,1'-cyclohexanes]...
Two series of new 7,9-disubstituted spirojulolidines 8a-d and 10a-e were synthesized by acid catalyzed intramolecular cyclization of N-(3-chloropropanoyl) spirodihydroquinolines 5a-d and N-carbethoxymethyl spirodihydroquinolines 7a-e using AlCl 3 and PPA, respectively. The spectroscopic analyses of intermediate compounds and the final spirojulolidines were discussed.
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