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17.2.2.1.5.1.1.8 Method 8: By Nucleophilic Substitution with Ammonia, Amines, and Related Nucleophiles

DOI: 10.1055/sos-SD-017-00553

Lindsley, C. W.; Layton, M. E.Science of Synthesis, (200417399.

The addition of ammonia to the 1,2,4-triazine ring is a valuable synthetic method.[‌197‌] Unlike the Chichibabin reaction for the addition of ammonia to pyridine, the introduction of ammonia at C5 of a 1,2,4-triazine occurs smoothly at room temperature and below. For example, the initial reaction of triazines with ammonia affords 2,5-dihydro adducts 198, which can be oxidized in situ by the addition of potassium permanganate to furnish 1,2,4-triazin-5-amines 199 (Scheme 77). Nucleofugal groups at C3 are not normally displaced by ammonia under these conditions.[‌197‌]

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