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Lord, George Harry (1957) An investigation of the properties of 1-phenylpyrazole-4-aldehyde and the compounds derived from it. Doctoral thesis, Northern Polytechnic.
The method of direct formylation with dimethylformamide and phosphoryl chloride has been extended to the pyrazole nucleus.
The isomeric aldoximes of 4-formyl-l-phenylpyrazole have been prepared and the syn- and anti-forms characterised by the action of n-butylamine on their acetyl derivatives.
The reaction between 4-formyl-l-phenylpyrazole and a representative series of Grignard reagents has been investigated. The resultant carbinols have been oxidised to the corresponding ketones, some of which have been reduced to give 4-alkyl-l- phenylpyrazoles.
The Claisen-Schmidt condensation has been used to prepare some pyrazole analogues of benzalacetophenone. These compounds have been treated with phenylhydrazine to give pyrazolyl- pyrazollnes, from which were prepared dipyrazolyls and a tripyrazolyl.
A number of the above pyrazoles have been examined spectroscopically, and as a result it has been found that any 4-substituent, with positions 3- and 5- vacant, always produced a maximum absorption at 10.5u.
The following new compounds have been prepared and characterised:
4-Formyl-1-methylpyrazole
4-Formyl -1 -methylpyrezol e- 2 : 4-dinitrophenylhydrazone
1-Methylpyrazole-4-carboxylic acid
4-Formyl-l-phenylpyrazoleayn -aldoxime
4 -Formyl -1-phenylpyrazole-anti-aldoxime
4 -Formyl -1-phenylpyraz ole-syn-acetylaldoxime
4-Fomyl-l-phenylpyrazole-anti-aeetylaldoxime
4 -Cyano-l-phenylpyrazole
4-Formyl-l-p-nitrophenylpyrazole l-p-Nitrophenylpyrazole-4-carboxylic acid
Di(l-phenyl-4-pyrazolyl) sulphoxide
Di(l-phenyl-4-pyrazolyl) sulphone
Methyl(l-phenyl-4-pyrazolyl)carbinol
Ethyl(l-phenyl*4-pyrazolyl)carbinol
n-Propyl(l-phenyl-4-pyrazolyl)carbinol
n-Butyl(l-phenyl-4-pyrazolyl)carbinol
isopropyl(l-phenyl-4-pyrazolyl)carbinol
tert. -Butyl (1-phenyl-4-pyraz olyl) carbinol
Phenyl(l-phenyl-4-pyrazolyl)carbinol
4 -Acetyl -l-phenylpyrazole-2:4-dinitrophenylhydrazone
Ethyl (l-phenyl-4-pyrazolyl) ketone
n-propyl (l-phenyl-4-pyrazolyl) ketone
n-Butyl (l-phenyl-4-pyrazolyl) ketone
isopropyl (l-phenyl-4-pyrazolyl) ketone
tert.-Butyl (l-phenyl-4-pyrazolyl) ketone
4-Ethyl-1-phenylpyrazole
4-n-Propyl-l-phenylpyrazole
4-n-Butyl-1-phenylpyrazole
4-n-Pentyl-l~phenylpyrazole
4-Propenyl-l-phenylpyrazole
A dimer of 4-propenyl-l-phenylpyrazole, viz. 2-methyl-l:I3- di(1-phenyl-4-pyrazolyl)-pent-2-ene
1-Phenyl-3-(1-phenyl-4-pyrazolyl)prop-2-en-l-one
3-phenyl-l-(1-phenyl-4-pyrazolyl)prop-2-en-l-one
1:3-Di (l-phenyl-4'-pyrazolyl)prop-2-en-l-one
1:3-Diphenyl-5-(1'-phenyl-4'-pyrazolyl)pyrazoline
1:5 -Diphenyl -3- (1' -phenyl-4' -pyrazolyl) pyrazoline
1-phenyl-3:5-di(1'-phenyl-4'-pyrazolyl)pyrazoline
1:1' :3-Triphenyl-4' :5-dipyrazolyl
1:1:5-Triphenyl-3:4z-dipyrazolyl
1-Phenyl-3:5-di(1-phenyl-4z-pyrazolyl)pyrazole
4-Formyl-1:1 3-triphenyl-4:5-dipyrazolyl
1:1' :3-Triphenyl-4:5 -dipyrazolyl-4-carboxylic acid
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