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Abstract The nitrogen‐heteroatom single bonds of 1,2‐azoles and isoxazolines underwent methylene insertion in the presence of CH2I2 (6 equiv.) and diethylzinc (3 equiv.) to produce a wide variety of the ring‐expanded six‐membered heterocycles. Density functional theory calculations suggest that the methylene insertion proceeds via cleavage of nitrogen‐heteroatom single bonds followed by ring closure.