Cascade Nucleophilic Attack/Addition Cyclization Reactions to Synthesize Oxazolidin-2-imines via ( Z )-2-Bromo-3-phenylprop-2-en-1-ols/3-phenylprop-2-yn-1-ols and Diphenyl Carbodiimides.

Two concise strategies to synthesize oxazolidin-2-imines by cascade nucleophilic attack/addition cyclization reactions of ( Z )-2-bromo-3-phenylprop-2-en-1-ols/3-phenylprop-2-yn-1-ols and diphenyl carbodiimides without a transition-metal catalyst have been developed. The reactions exhibited good substrate applicability tolerance, and a variety of substituted ( Z )-4-(( Z )-benzylidene)- N ,3-diphenyloxazolidin-2-imines were synthesized in moderate to excellent yields with good stereoselectivity. The reports also provided a convenient strategy to synthesize 3-phenylprop-2-yn-1-ols by ( Z )-2-bromo-3-phenylprop-2-en-1-ols. The economic and practical methods provide a great advantage for potential industrial synthesis of oxazolidin-2-imines.