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Synthesis and chemical reactivity of indenoisoxazoles
Author(s) -
Lemke Thomas L.,
Sawhney Kailash N.,
Lemke B. Kaye
Publication year - 1982
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570190229
Subject(s) - chemistry , hydroxylamine , hydrazine (antidepressant) , amine gas treating , isoxazole , ammonia , reactivity (psychology) , medicinal chemistry , alcohol , liquid ammonia , organic chemistry , medicine , alternative medicine , chromatography , pathology
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 p H 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.