Abstract Abstract New substituted dihydrospiro[(1H)quinoline‐2,1′‐cyclohexanes] were prepared by the internal alkene alkylation of N‐(1‐allylcyclohexanyl) ethylphenylamine obtained from the corresponding ketimine and allylmagnesium bromide. The 1‐allyl‐6‐ethyl‐4‐methyl‐3,4‐dihydrospiro[(1H)quinoline‐2,1′‐cyclohexane] undergoes an amino‐Claisen transposition (BF3 · Et2O) to afford the 8‐allyl‐6‐ethyl‐4‐methyl substituted spiroquinolines or a second internal alkylation reaction promoted by Brönsted acid (H2SO4) to give a new unnatural lilolidine spiroderivative. Keywords: Internal alkene Friedel‐Crafts alkylationamino‐Claisen transpositionspiroquinolines Acknowledgments This work was supported by the grant of the Colombian Institute for Science and Research (COLCIENCIAS, projects: 1102‐05‐11429). Thanks are also due to Dr. F. Zubkov (Organic Chemistry Department of the Russian Peoples Friendship University) for providing 1H NMR spectra.