Objective Pyrazolone and hydroxyindole structures are two very important pharmacophore, which occupy a very important position in medicinal chemistry. Among them, pyrazolone is a kind of five membered heterocyclic compounds containing N-N bond. It has become one of the most important nitrogen heterocycles in heterocycles due to its wide application in medicinal chemistry and functional materials. At the same time, hydroxyindole derivatives have unique physiological anticancer activity and analgesic effects due to their unique chemical structure. Isatin is an oxidation product of indigo, found in plants of the genus Isatis, and is a metabolic derivative of adrenaline in the human body. In view of the importance of pharmacophore combination strategy in drug research and development, the organic combination of these two pharmacophore will lay an important molecular foundation for drug research and development. Methods Considering the important application of SNV reaction in C-C bond coupling, in this paper, starting from the 4-position monosubstituted pyrazolone, a variety of chiral alkenylpyrazolone adduct were obtained through the SNV reaction between it and the isatin-derived nitroalkenes. The optimal reaction conditions were determined by screening factors such as catalysts, solvents, and temperature. Under the optimal reaction conditions, substrate expansion of structurally diverse pyrazolone compounds was achieved, and the resulting products were characterized and analyzed by 1H NMR, 13C NMR, HRMS, and other methods to determine their structures. Results This synthesis strategy constructs a series of chiral alkenyls containing a tetrasubstituted stereoisomeric center with a hydroxyindole moiety, which have high yields (excellent regioselectivity (E: Z >20:1) and good enantioselectivity (up to 86% ee). Conclusion These new alkenylpyrazolone adduct are expected to provide material support for the search for new lead compound.