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Synthesis and chemical reactivity of indenoisoxazoles

 

作者: Thomas L. Lemke,   Kailash N. Sawhney,   B. Kaye Lemke,  

 

期刊: Journal of Heterocyclic Chemistry  (WILEY Available online 1982)
卷期: Volume 19, issue 2  

页码: 363-368

 

ISSN:0022-152X

 

年代: 1982

 

DOI:10.1002/jhet.5570190229

 

出版商: Wiley‐Blackwell

 

数据来源: WILEY

 

摘要:

AbstractTreatment 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 basicpH gave6which upon cyclization gave the isomeric 3‐t‐butylindeno[1,2‐c]isoxazol‐4‐one (7). Compound7was readily reduced to amine12by 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 to15and16with sodium in liquid ammonia and alcohol. Surprisingly, the amine3obtained from isoxazole2gave reduction product15from a sodium‐liquid ammonia reduction and not the expected product18.Spectral evidence fo

 

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