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

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概要

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• 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 C^4-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).

• 公益社団法人日本薬学会の論文
• 1985-04-25

著者

• 林 英作

  Shizuoka College of Pharmacy

• 東野 武郎

  Shizuoka College of Pharmacy

• 林 英作

  School Of Pharmaceutical Sciences University Of Shizuoka

• 竹元 万寿美

  Shizuoka College of Pharmacy

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