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STUDY OF 4-MONO- AND 4,4-DISUBSTITUTED-3-IMINO-2-BENZOYL-5-PYRAZOLONES

 

作者: Paul E. Gagnon,   Jean L. Boivin,   Paul A. Boivin,   Hugh M. Craig,  

 

期刊: Canadian Journal of Chemistry  (NRC Available online 1952)
卷期: Volume 30, issue 1  

页码: 52-61

 

ISSN:0008-4042

 

年代: 1952

 

DOI:10.1139/v52-007

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

4-Mono- and 4,4-disubstituted-3-imino-2-benzoyl-5-pyrazolones have been prepared from the corresponding ethyl mono- or disubstituted cyanoacetates and N-benzoylhydrazine. The presence of the imino group in 4,4-disubstituted-3-imino-2-benzoyl-5-pyrazolones was ascertained by the hydrolysis of 4,4-dibenzyl-3-imino-2-benzoyl-5-pyrazolone into 4,4-dibenzyl-3-oxo-2-benzoyl-5-pyrazolone. In order to prove that the benzoyl group in these pyrazolones was not in Position 1, the synthesis of 4-benzyl-3-amino-1-benzoyl-5-pyrazolone was attempted from 4-benzyl-3-carbethoxy-1-benzoyl-5-pyrazolone through a Curtius degradation of the 3-carbethoxy substituent into a 3-amino group. It was found that the 1-benzoyl group was hydrolyzed at the same time as the 3-carbethoxyamino substituent. The ultraviolet absorption spectra of all these compounds are reported and discussed briefly.

 

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