Reactions of 3-Benzoyl-3,4-dihydro-2-methyl-4-quinazolinecarbonitrile(2-Methylquinazoline Reissert Compound) with Acid, Base, Sodium Hydride, and Electrophiles

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概要

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• Acid hydrolysis of 3-benzoyl-3,4-dihydro-2-methyl-4-quinazolinecarbonitrile (1_1,2-methyl-quinazoline Reissert compound) resulted in the formation of the oxazole (1_3). Alkaline hydrolysis gave 2-methylquinazoline (1_2) and benzoic aicd (8). The anion (D^1), generated from 1_1 and NaH in dimethylformamide (DMF), underwent decomposition to give the ketone (1_4) and the cyanoquinazoline (1_5) together with by-products 1_2 and O-benzoylbenzoin (9). Compound 1_1 reacted with aromatic aldehydes (10a-c) in the presence of NaH to give the benzoates (1_6a-c) and by-products 1_2 and 1_5. Alkylation (or arylation) with alkyl (or aryl) halides (11a, b) afforded the corresponding 4-substituted derivatives (1_9a, b) and a by-product 1_4.The reactivities of 1_1. and 3-benzoyl-3,4-dihydro-4-quinazolinecarbonitrile (2_1,quinazoline Reissert compound) are compared.

• 社団法人日本薬学会の論文
• 1988-03-25

著者

• 東野 武郎

  School Of Pharmaceutical Sciences University Of Shizuoka

• 丹治 健一

  School of Pharmaceutical Sciences, University of Shizuoka

• 佐藤 進

  Central Research Laboratories, S S Pharmaceutical Co., Ltd.,

• 宮下 晶

  School Of Pharmaceutical Sciences University Of Shizuoka

• 佐藤 進

  Department Of Pharmacology Pharmaceutical Institute Tohoku University

• 丹治 健一

  School Of Food & Nutritional Sciences University Of Shizuoka

• 香取 達彦

  Central Research Laboratories, SS Pharmaceutical Co., Ltd.

• 菅 浩貴

  School of Pharmaceutical Sciences, University of Shizuoka

• 菅 浩貴

  School Of Pharmaceutical Sciences University Of Shizuoka

• 香取 達彦

  Central Research Laboratories S S Pharmaceutical Co. Ltd.

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