82501-30-2Relevant academic research and scientific papers
Synthesis and Chemical Reactivity of Indenoisoxazoles
Lemke, Thomas L.,Sawhney, Kailash N.,Lemke, B. Kaye
, p. 363 - 368 (2007/10/02)
Treatment of 2-pivaloyl-1,3-indandione (1) with hydroxylamine under acidic conditions, results in formation of 8-t-butylindenoisoxazol-7-one (2) while treatment of the triketone with hydroxylamine at neutral or basic pH gave 6 which upon cyclization gave the isomeric 3-t-butylindenoisoxazol-4-one (7).Compound 7 was readily reduced to amine 12 by treatment with hydrazine or hydrogen over platinum.The amine, although quite unreactive, was converted to 3-t-butylindenopyrazol-4-one (13) with hydrazine or reduced to 15 and 16 with sodium, in liquid ammonia and alcohol.Surprisingly, the amine 3 obtained from isoxazole 2 gave reduction product 15 from a sodium-liquid ammonia reduction and not the expected product 18.Spectral evidence for each of the structures is discussed.
