95113-40-9Relevant academic research and scientific papers
Reissert Compound Studies. LXI. Preparation and Reactions of Quinazoline Di-Reissert Compounds
Hahn, Jung-Tai,Popp, Frank D.
, p. 1357 - 1372 (2007/10/02)
Various di-Reissert compounds and analogs were prepared from quinazoline by use of trimethylsilyl cyanide together with a catalytic amount of anhydrous aluminum chloride.Reactions of these quinazoline di-Reissert compounds are reported.
Reactions of the Anion of Quinazoline Reissert Compound (3-Benzoyl-3,4-dihydro-4-quinazolinecarbonitrile) with Electrophiles
Higashino, Takeo,Kokubo, Hiroyasu,Hayashi, Eisaku
, p. 950 - 961 (2007/10/02)
Reactions of the quinazoline Reissert compound (2) with various electrophiles in the presence of sodium hydride in N,N-dimethylformamide were investigated.The reactions with aldehydes (3) and ketones (12) gave α-aryl (or alkyl)-(7) and α-alkyl-α-aryl (or alkyl)-4-quinazolinylmethyl benzoates (16), respectively.The reaction with ?-deficient heteroaromatics (10a-c) gave 4-heteroarylquinazolines (20a-c).Alkylation (or arylation) with alkyl (or aryl) halides (23a-c) afforded 4-substituted 3-benzoyl-3,4-dihydro-4-quinazolinecarbonitriles (24a-c).The reaction with dimethyl acetylenedicarboxylate proceeded in two ways, giving dimethyl 3-phenylpyrroloquinazoline-1,2-dicarboxylate (27) and dimethyl 3-benzoyl-4-cyano-1,2,3,4-tetrahydro-2,4-ethenoquinazoline-9,10-dicarboxylate (28).The reaction with 2-alkenonitriles (29a,b) resulted in the formation of 2-benzoyl-3-(4-quinanolinyl)alkanonitriles (32a,b).Keywords - rearrangement; substitution; 1,3-dipolar addition; quinazoline Reissert compound anion; α-substituted 4-quinazolinylmethyl benzoate; 4-heteroarylquinazoline; 4-substituted 3,4-dihydro-4-quinazoline carbonitrile; pyrroloquinazoline; 2,4-ethenoquinazoline; 2-benzoyl-3-(4-quinazolinyl)alkanonitrile
Reaction of 4-Aroylquinazolines with Sodium Hydroxide: Aryl Migration to Give 4-Aryl-3,4-dihydro-4-quinazolinecarboxylic Acids and Formation of Quinazoline and Aroic Acids
Higashino, Takeo,Takemoto, Masumi,Hayashi, Eisaku
, p. 1351 - 1359 (2007/10/02)
4-Aroylquinazolines (3) were prepared in good yields by alkaline hydrolysis of α-aryl-4-quinazolinylmethyl benzoates (15), followed by oxidation.The reaction of 3 with sodium hydroxide in dimethyl sulfoxide(DMSO) was found to proceed in two ways.One path is the aryl migration to lead to 4-aryl-3,4-dihydro-4-quinazolinecarboxylic acids (4), and the other is the fission of the C4-CO bond to yield quinazoline (5) and aroic acids (6). Potassium ferricyanide oxidized the carboxylic acids 4 to the corresponding 4-arylquinazolines (14) with elimination of carbon dioxide. Reaction of 4-benzoylquinazoline (3a) with methylmagnesium iodide did not result in the migration, but instead yielded of α-methyl-α-phenyl-4-quinazolinemethanol (18) and 3,4-dihydro-α,4-dimethyl-α-phenyl-4-quinazolinemethanol (19).
Preparation and Reactions of Quinazoline Reissert Compound (3-Benzoyl-3,4-dihydro-4-quinazolinecarbonitrile)
Higashino, Takeo,Kokubo, Hiroyasu,Hayashi, Eisaku
, p. 3900 - 3905 (2007/10/02)
The benzoylation of 3,4-dihydro-4-quinazolinecarbonitrile (3) with benzoyl chloride in pyridine gave quinazoline Reissert compound (1, 3-benzoyl-3,4-dihydro-4-quinazolinecarbonitrile) in 82percent yield. The alkaline hydrolysis of 1 in methanol resulted in the formation of quinazoline (2) and benzoic acid (4).Acid hydrolysis gave 2-benzamido-2-(2-aminophenyl)acetonitrile (6), 4, and 2.The HCl salt of 1 existed predominantly in the cyclic amidinium structure of the type 8.Compound 1reacted with sodium hydride in dimethylformamide to yield 4-quinazolinecarbonitrile (9), α-phenyl-4-quinazolinylmethyl benzoate (10) and O-benzoylbenzoin (11). In the present paper we compare the chemical properties of 1 with those of isoquinoline Reissert compound (13, 2-benzoyl-1,2-dihydro-1-isoquinolinecarbonitrile). Keywords --- quinazoline Reissert compound; cyclic amidinium cation; alkaline hydrolysis; acid hydrolysis; quinazoline Reissert compound anion; acetonitrile derivative; 4-quinazolinecarbonitrile; 4-quinazolinylmethyl benzoate derivative
