Piskala, A.; Gut, J.; Sorm, F. published the artcile< Chemistry of 1,2,4-triazine. VIII. Reaction of 3,5,6-trichloro-1,2,4-triazine with simple nucleophiles>, Application of C3H2BrN3O2, the main research area is trichlorotriazine reaction nucleophile; chlorotriazine reaction nucleophile; triazine trichloro reaction nucleophile.
3,5,6-Trichloro-1,2,4-triazine (I) was prepared from 6-bromo-1,2,4-triazine-3,5(2H,4H)-dione and refluxing POCl3. With NH3-MeOH, I gave 5-amino-3,6-dichloro-1,2,4-triazine (II). With 1 mole NaOMe-MeOH or NaHCO3 in aqueous MeOH, I gave 3,6-dichloro-5-methoxy-1,2,4-triazine (III). With 2 moles NaOMe-MeOH, I gave a mixture of 6-chloro-3,5-dimethoxy- (IV) and 3-chloro-5,6-dimethoxy-1,2,4-triazine (V) while with excess NaOMe-MeOH, 3,5,6-trimethoxy-1,2,4-triazine (VI) was obtained. Reaction of III with NH3-MeOH gave II. With NaOMe-MeOH, II gave 5-amino-3-chloro-1,2,4-triazine. With HCl-MeOH, II gave 5-amino-6-chloro-3-methoxy-1,2,4-triazine (VII). Hydrogenolysis of II in dioxane over 10% Pd/C in the presence of N-ethylpiperidine gave a mixture of 5-amino-1,2,4-triazine and 5-amino-3-chloro-1,2,4-triazine. A similar hydrogenolysis of VII gave 5-amino-3-methoxy-1,2,4-triazine. VI refluxed in HCl-MeOH gave 6-methoxy-1,2,4-triazine-3,5(2H,4H)-dione. V was resistant to hydrogenolysis while IV gave 3,5-dimethoxy-1,2,4-triazine. In the above experiments, the positional reactivity of the 1,2,4-triazine ring system decreased in the order 5>3>6 with neutral nucleophiles and in the order 5>6>3 with anionic nucleophiles.
Collection of Czechoslovak Chemical Communications published new progress about Ammonolysis. 4956-05-2 belongs to class pyrimidines, and the molecular formula is C3H2BrN3O2, Application of C3H2BrN3O2.
Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia