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

1952 ◽  
Vol 30 (1) ◽  
pp. 52-61 ◽  
Author(s):  
Paul E. Gagnon ◽  
Jean L. Boivin ◽  
Paul A. Boivin ◽  
Hugh M. Craig

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.

1952 ◽  
Vol 30 (11) ◽  
pp. 904-914 ◽  
Author(s):  
Paul E. Gagnon ◽  
Jean L. Boivin ◽  
Alexander Chisholm

1,4-Dimethyl-3-amino-5-pyrazolone and 4-methyl- and 4-ethyl-3-amino-1-phenyl-5-pyrazolones were synthesized from α-keto esters and methyl- and phenylhydrazines. The hydrazones first obtained were transformed into pyrazolones having a carbethoxy group in position 3, which was converted into an amino group by a Curtius degradation. 2,4-Dimethyl-3-amino-5-pyrazolone was obtained directly from methylhydrazine and ethyl α-cyanopropionate. A series of 3-imino-2-methyl-5-pyrazolones monosubstituted in position 4 with pentyl, hexyl, heptyl, and octyl groups and another series disubstituted in position 4 with butyl, hexyl, and heptyl groups were also prepared from the corresponding mono- and disubstituted cyanoacetates and methylhydrazine.The ultraviolet absorption spectra were determined in neutral and acid medium.


1951 ◽  
Vol 4 (1) ◽  
pp. 93 ◽  
Author(s):  
SJ Angyal ◽  
WK Warburton

By the study of ultraviolet absorption spectra and comparison with methyl derivatives of known structure it is shown that the two forms of arylsulphonylbenzamidines described by Barber (1943) are tautomers, the more stable one having structure I. In dilute solution, sulphathiazole is found to be mainly X, and sulphapyridine a mixture of XIII and XIV in a ratio which depends on the solvent and can be influenced by changes on the p-amino group. Bands of the spectra are assigned to structural features of these molecules.


2013 ◽  
Vol 779 (1) ◽  
pp. 40 ◽  
Author(s):  
Yu-Jong Wu ◽  
Hui-Fen Chen ◽  
Shiang-Jiun Chuang ◽  
Tzu-Ping Huang

1950 ◽  
Vol 187 (1) ◽  
pp. 299-312
Author(s):  
R.L. Sinsheimer ◽  
J.F. Scott ◽  
J.R. Loofbourow

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