Isoxazole derivatives. V. Reaction of hydrazine on 5-aminoisoxazoles. 1 was written by Kano, Hideo. And the article was included in Yakugaku Zasshi in 1953.Recommanded Product: Isoxazol-5-amine This article mentions the following:
O.N:CR.CR’:CNH2 (I, R = Me) (IA) (5 g.) and 5 g. 50% N2H4.H2O heated 2.5 hrs. on a water bath, and the product filtered and recrystallized from H2O give 2.5 g. NH.NH.CO.CR’:CR (II, R = Me) (IIA), prisms, m. 271-2°; 1 g. IIA and 2 ml. Ac2O boiled 30 min., cooled, a small amount of water added, and the precipitate recrystallized from MeOH give NAc.NAc.CO.CR’:CR (III, R = Me) (IIIA), needles, m. 54°. Similarly are prepared the following derivatives of I, II, and III, resp. (R, R’, and m.p. given): Me, Et, 89-90°, 229-30°, 57°; Me, Pr, 77-8°, 211-2°, 40-1°; Me, PhCH2, 79°, 230-1°, 69°; (R + R’ =) (CH2)4, 119° 285-6° (decomposition), 79-80°. IA (5 g.) and 5 g. PhNHNH2 heated 8 hrs. at 100° and the product extracted with Et2O give 1.9 g. 4,4′-bis(1-phenyl-3,4-dimethyl-5-pyrazolone), prisms, m. 165°. 3-Methyl-, 3-phenyl-, 3-benzyl-4-phenyl-, 3-ethyl-4-methyl-, and 3-butyl-4-propyl-5-aminoisoxazole with N2H4.H2O or PhNHNH2 do not give pyrazolone derivatives AcCHMeCONH2 (0.5 g.) and 1 g. 50% N2H4.H2O heated 15 min. on a water bath and the product recrystallized from alc. give IIA, m. 270-1°. In the experiment, the researchers used many compounds, for example, Isoxazol-5-amine (cas: 14678-05-8Recommanded Product: Isoxazol-5-amine).
Isoxazol-5-amine (cas: 14678-05-8) belongs to isoxazole derivatives. Isoxazoles also form the basis for a number of drugs, including the COX-2 inhibitor valdecoxib (Bextra) and a neurotransmitter agonist AMPA. Isoxazoles are potent isosteres of pyridine and have been found to inhibit voltage-gated sodium channels for pain control, for the construction of tetracycline antibiotic derivatives, and as a therapeutic agent for depression.Recommanded Product: Isoxazol-5-amine
Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem