110212-02-7Relevant academic research and scientific papers
Studies on Pyrazolopyrimidine Derivatives. XVI. Preparation of Reissert Compounds from Condensed Pyrimidine Systems Catalyzed by Lewis Acids
Higashino, Takeo,Sato, Susumu,Miyashita, Akira,Katori, Tatsuhiko
, p. 4803 - 4812 (2007/10/02)
Among various Lewis acids, aluminium chloride (AlCl3) was the most effective catalyst for the formation of the Reissert compound (21a,5-benzoyl-4,5-dihydro-1-phenyl-1H-pyrazolo-pyrimidine-4-carbonitrile) of 1-phenyl-1H-pyrazolopyr
Studies on Pyrazolopyrimidine Derivatives. XIV. Preparation and Reactions of 1-Phenyl-1H-pyrazolo-pyrimidine Reissert Compound
Higashino, Takeo,Sato, Susumu,Miyashita, Akira,Katori, Tatsuhiko
, p. 4569 - 4576 (2007/10/02)
The Reissert reaction of 1-phenyl-1H-pyrazolopyrimidine (4) in anhydrous methylene chloride using benzoyl chloride, trimethylsilyl cyanide, and a catalytic amount of aluminium chloride gave the corresponding Reissert compound (3, 5-benzoyl-4,5-dihydro-1-phenyl-1H-pyrazolopyrimidine-4-carbonitrile) in 95percent yield.The alkaline hydrolysis of 3 in methanol resulted in the formation of 4, benzoic acid (7), and the 4,4'-dimer (9) of (4).The acid hydrolysis in dimethyl sulfoxide and in methanol proceeded with ring fission to give 5-amino-α-benzamido-1-phenyl-1H-pyrazole-4-acetonitrile (13), the acetamide (14), and the acetate (15).Compound 3 reacted with sodium hydride in dimethylformamide to give 4, 9, 1-phenyl-1H-pyrazolopyrimidine-4-carbonitrile (20), α,1-diphenyl-1H-pyrazolopyrimidin-4-ylmethyl benzoate (21), and O-benzoylmandelonitrile (22).In the present paper, we compare the chemical properties of 3 with those of the isoquinoline Reissert compound (1, 2-benzoyl-1,2-dihydro-1-isoquinolinecarbonitrile).Keywords-pyrazolopyrimidine Reissert compound; preparation; chemical property; hydrolysis; pyrazoleacetonitrile; carbanion; rearrangement; pyrazolopyrimidinemethanol
