Preparation and reactivity of acetoacetonitrile dianion was written by Vinick, Fredric J.;Pan, Yolanda;Gschwend, Heinz W.. And the article was included in Tetrahedron Letters in 1978.Application In Synthesis of 5-Methylisoxazole This article mentions the following:
The title dianion (I) was prepared by treating 5-methylisoxazole (II) with 2 equiv LiN(CHMe2)2 in THF at -10°. I underwent alkylation by alkyl halides RX to give unstable RCH2COCH2CN; immediate NaBH4 reduction of the products gave RCH2CH(OH)CH2CN (R = allyl, Pr, PhCH2) in 49-52% overall yield from II. I with RCOR1 (R = H, R1 = 4-ClC6H4; R = R1 = Ph) gave 44-82% RC(OH)R1CH2CH(OH)CH2CN. I with PhCN gave 24% PhC(NH2):CHCOCH2CN. I with RC6H4CN (R = 4-MeO, -Cl, 3-Me) gave 62-5% of the corresponding 6-(RC6H4)-substituted 2-amino-4(1H)-pyridones. In the experiment, the researchers used many compounds, for example, 5-Methylisoxazole (cas: 5765-44-6Application In Synthesis of 5-Methylisoxazole).
5-Methylisoxazole (cas: 5765-44-6) belongs to isoxazole derivatives. Isoxazoles are aromatic heterocycles containing an N–O bond. Isoxazoles are commonly used as enaminoketone or β-diketone surrogate. The most common methods for N–O bond cleavage in isoxazoles are hydrogenation with palladium or platinum catalysts or with Raney Ni. Recent developments have shown that Mo(CO)6 efficiently cleaves the N–O bond in isoxazoles.Application In Synthesis of 5-Methylisoxazole
Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem