Cycloadditions in combination with multicomponent reactions are among the most valuable synthetic tools used by organic chemists to construct cyclic and heterocyclic compounds in a straightforward way. Although cycloadditions, such as the Diels--Alder reaction, are mainly covered in basic and advanced organic courses for undergraduate students, few experiments are reported in the literature for undergraduate organic chemistry laboratories. Here we describe a new experiment to illustrate the multicomponent imino-Diels-Alder cycloaddition to obtain a tetrahydroquinoline derivative under green chemistry conditions. Different synthesis procedures, including solvent-free reactions, microwave assisted reactions, use of a deep eutectic solvent, and star anise oil as starting material, were evaluated by students. The structure of the synthesized compound was confirmed by NMR spectroscopy ([superscript 1]H, APT, COSY, HSQC), IR spectroscopy, mass spectrometry, and melting point analysis. In addition, the stereochemistry was also proposed by students based on the NMR data.