87412-75-7Relevant academic research and scientific papers
Studies on Pyrazolopyrimidine Derivatives. XIII. Aryl Migration of 4-Aroyl-1H-pyrazolopyrimidines to 4-Aryl-4,5-dihydro-1H-pyrazolopyrimidine-4-carboxylic Acids
Higashino, Takeo,Matsushita, Yasuhiko,Takemoto, Masumi,Hayashi, Eisaku
, p. 3951 - 3958 (2007/10/02)
When a mixture of 4-aroyl-1-phenyl-1H-pyrazolopyrimidines (3) and sodium hydroxide in dimethyl sulfoxide (DMSO) was stirred for 1 h at room temperature, migration of the aryl group to the 4-position occurred, i.e., the benzilic acid rearrangement,
Aryl Coupling Reactions of Pyrazolopyrimidin-4-yl Radicals
Press, Jeffery B.,Eudy, Nancy H.,Morton, George O.
, p. 4605 - 4611 (2007/10/02)
4-Arylpyrazolopyrimidines (4) were the subjects of a synthetic investigation in order to evaluate their biological activity.Attempts to prepare 4 from 4-aminopyrazolopyrimidines (5) via classical Gomberg-Bachmann-Hey aryl coupling conditions failed.Conversion of 5 to 4 was accomplished by diazotiazation of 5 using alkyl nitrites with an acid catalyst in aromatic solvents.Isomer distribution of the aryl-coupled products 4 was that predicted for a radical intermediate (ortho > meta ca. para); isomer structures were assigned by a detailed 1H NMR analysis.Unusual fragmentation products 17 and 18 were isolated during the course of investigations.These oxadiazoles probably arise from collapse of intermediate pyrazolopyrimidin-4-yl radicals 15.
