Abstract: Comprehensive organic chemistry experiments constitute a fundamental component of chemical education, serving to significantly enhance undergraduates’ basic laboratory skills while deepening their understanding of specialized knowledge. This foundation proves crucial for future academic pursuits and professional development. We present herein an integrated organic chemistry experiment involving the palladium-catalyzed tandem cyclization of 4-vinylbenzoxazinone and indene-2-carbaldehyde to synthesize 12-vinyl-7,12-dihydrobenzo[b]indeno[1,2-e]azepine. The product structure was characterized using high-resolution mass spectrometry (HRMS), along with ¹H and ¹³C nuclear magnetic resonance spectroscopy.

Key words: Comprehensive organic chemistry experiment, Tandem cyclization, Palladium catalysis, Synthesis and structural characterization