Preparation and Reactions of Quinazoline Reissert Compound (3-Benzoyl-3,4-dihydro-4-quinazolinecarbonitrile)

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概要

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• 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 82% 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 1 reacted 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).

• 社団法人日本薬学会の論文
• 1984-10-25

著者

• 小久保 宏恭

  Specialty Chemicals Research Center Shin-etsu Chemical Co. Ltd.

• 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

• 小久保 宏恭

  Shizuoka College of Pharmacy

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