The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Titanium(0) reagents. III. A convenient preparation of 4-pyridinamine derivatives》. Authors are Malinowski, Marek; Kaczmarek, Lukasz.The article about the compound:3,5-Dimethyl-4-nitropyridine 1-oxidecas:14248-66-9,SMILESS:O=[N+](C1=C(C)C=[N+]([O-])C=C1C)[O-]).Application In Synthesis of 3,5-Dimethyl-4-nitropyridine 1-oxide. Through the article, more information about this compound (cas:14248-66-9) is conveyed.
Ti(0) slurry, easily accessible by the reduction of TiCl4 with LiAlH4 or Mg in THF, is an excellent reagent for the reduction of N-nitropyridine N-oxides, e.g., I (R = H, Me, F, Cl) to 4-aminopyridines, e.g., II. The reaction proceeds smoothly and fast at room temperature giving the amines in >90% yields.
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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem