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17.2.2.1.5.1.3.1.2 Variation 2: Reactions of Alkoxy-1,2,4-triazines with Nucleophiles

DOI: 10.1055/sos-SD-017-00553

Lindsley, C. W.; Layton, M. E.Science of Synthesis, (200417404.

Alkoxy groups bound to a 1,2,4-triazine ring are readily exchanged upon treatment with amines or hydrazines to provide the corresponding 1,2,4-triazinamines 211 or hydrazino-1,2,4-triazines 212, respectively (Scheme 87). Yields are typically >80%.[‌1‌,‌11‌,‌79‌] In the case of 3-methoxy-1,2,4-triazine (210, OR1=3-OMe), for example, a reaction with hydrazine affords the corresponding 3-hydrazinyl derivative 212 (R2NHNH=3-NH2NH) in 82% yield.

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