A metal-free protocol for accessing both α and δ-carboline derivatives, starting from a common indolylchalcone oxime ester precursor is reported. The reaction involves mild conditions and uses a regiodivergent approach. DDQ is used as a switching agent in selectively generating a and d-carboline derivatives in good to moderate yields. The present methodology described a versatile pathway to furnish -carboline from relatively stable 2-amino indole derivatives and 3-bromopropenal. High substrate tolerance, nonmetallic, more efficient and mild condition reaction are important aspects.