Thomas L. Lemke, Kailash N. Sawhney and, B. Kaye Lemke
1982
Citations
0
Influential Citations
13
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
Treatment of 2-pivaloyl-1,3-indandione (1) with hydroxylamine under acidic conditions, results in formation of 8-t-butylindeno[1,2-c]isoxazol-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-butylindeno[1,2-c]isoxazol-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-butylindeno[1,2-c]pyrazol-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.