In this paper, we have established an operationally convenient protocol for the rapid construction of polysubstituted methyleneindene and quinoline derivatives under mild conditions. This new synthetic method is achieved through the conversion of acetyl-substituted methylenecyclopropanes with TsOH ⋅ H 2 O and ortho-amino-substituted methylenecyclopropanes with aromatic aldehyde and TsOH ⋅ H 2 O, respectively. A variety of transformations of the obtained products was demonstrated. The plausible reaction mechanisms were also proposed.