Oxazolidinone represents a class of most important five‐membered cyclic carbamates. They are of great significance for modern organic synthesis and are widespread as pharmacologically active compounds. This review summarizes recent advances in the chemistry of 2‐oxazolidinones, with an emphasis on their synthesis, employing different catalytic systems or catalyst‐free conditions, as well as on their ring‐opening transformations through decarboxylative coupling, covering the period from 2010 to early 2021. Detailed mechanistic aspects are highlighted, hoping to help researchers to explore the hidden opportunities for reaction discoveries.