73112-03-5Relevant 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
Ring Fission of Quinazolines by Means of the Reissert Reaction
Higashino, Takeo,Kokubo, Hiroyasu,Goto, Ayako,Takemoto, Masumi,Hayashi, Eisaku
, p. 3690 - 3694 (2007/10/02)
Under the Reissert reaction conditions, quinazoline (1a) afforded 2'-formylbenzanilide (2a), o-aminobenzaldehyde (3a), and N-formylbenzamide (4).Similarly, 4-methyl- (1b) and 4-ethoxyquinazoline (1c) gave the corresponding benzanilides 2b and 2c, respectively, o-aminoacetophenone (3b, from 1b), and benzamide (5).It was confirmed that the same results were obtained in the absence of the cyanide ion.A substituent at the 2-position prevented the ring fission, and only the corresponding N3-benzoyl pseudo-base (14) was obtained.The generality of the ring fission was shown by the reactions of 1-phenyl-1H-pyrazolopyrimidine (6) and 3-phenyl-3H-1,2,3-triazolopyrimidine (8), giving 5-amino-1-phenyl-1H-pyrazole-4-carbaldehyde (7) and 5-amino-1-phenyl-1H-1,2,3-triazole-4-carbaldehyde (9), respectively.Keywords - 4-substituted quinazoline; 1H-pyrazolopyrimidine; 3H-1,2,3-triazolopyrimidine; 2'-acylbenzanilide; 2-aminophenyl alkyl ketone; N-formylbenzamide; ring fission.
