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A tandem CuAAC/ring cleavage/[4 + 2] annulation reaction of terminal ynones, sulfonyl azides, and oximes has been developed to synthesize functionalized dihydrooxazines under mild conditions. In particular, intermediate N-sulfonyl acylketenimines are the first example of a 4π-system participating in [4 + 2] cycloadditions, and dihydrooxazines can convert to 2-aminopyridines through ring cleavage under basic conditions.