The azaindoline skeleton exists in a wide range of bioactive molecules and natural products, and has significant biological and pharmaceutical activities. The synthesis of these compounds has attracted great attention from chemists. However, due to the electron-deficient nature of the pyridine ring where the nitrogen atom is located, many traditional methods for the synthesis of indoline cannot effectively construct the azaindoline skeleton. In recent years, chemists have been exploring the synthesis of azaindoline skeleton and have made some progress. According to the different reaction types, the synthesis of azaindolines in recent years and the key reaction mechanisms are reviewed and discussed, and the future development prospect of this research field is prospected.