Abstract: In contrast to conventional functional group transformation chemistry, skeletal editing strategies enable the rapid conversion of one complex molecule into another, thereby facilitating structural diversity in synthesis. However, undergraduate education—whether theoretical or experimental—has yet to incorporate this knowledge. This experiment introduces skeletal editing, a cutting-edge research field, into undergraduate laboratory teaching. Through a formal "nitrogen deletion and carbon insertion" process, a novel method for converting isoquinoline to naphthaldehyde was developed. The experiment integrates multiple operations from organic chemistry laboratory teaching, offering advantages such as short reaction time (1.5 h), cost-effective and readily available starting materials, and straightforward procedures. The product structure was confirmed through NMR spectroscopy, X-ray single-crystal diffraction, high-resolution mass spectrometry, and melting point analysis. This experiment not only enhances students’ understanding of skeletal editing—its definition, applications, and synthetic challenges—but also deepens their comprehension of the Diels-Alder reaction and reinforces fundamental laboratory techniques for separation and analysis. It fosters students’ ability to analyze and solve problems while stimulating their research interest and nurturing innovative thinking.

Key words: Skeletal editing, Diels-Alder cycloaddition, Rearrangement, Experimental teaching