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Lindsley, C. W.; Layton, M. E., Science of Synthesis, (2004) 17, 399.
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]
Meeeee 88 Meeeeeeee ee 8-Meeeeeeeeeeee 8,8,8-Meeeeeeee eeee Meeeeee[888]
M8 | M8 | Meeee (%) ee 888 | Mee |
---|---|---|---|
M | M | 88 | [888] |
Me | M | 88 | [888] |
Me | M | 88 | [888] |
M | Me | 88 | [888] |
MMe | M | 88 | [888] |
MM8 | M | 88 | [888] |
MM8 | Me | 88 | [888] |
MMe | M | 88 | [888] |
Me | Me | 88 | [888] |
Meeeeeeeeeee Meeeeeeee
8-Meeeeeeeeeeeee-8,8,8-eeeeeee-8-eeeee (888, M8 = MMe; M8 = M):[888]
8-Meeeeeeeeeeeee-8,8,8-eeeeeeee (8.88 e, 88 eeee) eee eeeee ee eeeee eeeeeeee ee e eeee ee MMeM8 (8 e) ee eee eee MM8 (888 eM) ee −88°M eeee eeeeeeee. Meeee 88 eee, eee MM8 eee eeeeeeeeee, eee eee eeeeeee eee eeeeeeeee eeee eee eMeMM (88 eM). Meeeeee ee eee eeeeeee eee eeeeeeeeeeeeeee ee eee eeeeeee (MeMM) eeeeeeee eee eeeee eeeeeeee; eeeee: 8.8 e (88%); ee 888–888°M.
References
[197] | Meeeeeee, M.; eee eee Meee, M. M., Meeeeeeee, (8888), 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88e8, 888.
- 8.Meeeee-Meee, (8888) M 8e, 888.