Studies on 4 (1H)-Quinazolinones. III. Some Derivatizations of 2-Ethoxycarbonylalkyl-1-substituted-4 (1H)-quinazolinones

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概要

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• Reactions of 2-(substituted-amino) benzamide (1) with ethyl chloroformylformate (2), ethyl chloroformylacetate (3), and ethyl 2-chloroformylpropionate (4) gave 1-substituted 4 (1H)-quinazolinones (5,6,and 7,respectively) having an ethoxycarbonyl group on the substituent at position 2. 2-Ethoxycarbonyl-1-methyl-4 (1H)-quinazolinone (5b) was converted to the carboxylic acid 14,the hydroxamic acid 16,the amide 18,and the nitrile 19. The nitrile 19 was allowed to react with various nucleophiles to give 1-methyl-4 (1H)-quinazolinones (17,20,21,and 22) having a substituted heteroatom at position 2. The reaction of 19 with sodium azide gave 1,2-dihydro-4-hydroxy-1-methyl-2-(5H-tetrazol-5-ylidene)-quinazoline (25) which is the 1,3-dipolar addition product to the cyano group. The intramolecular ring closures of 5,6,and 7 having an alkoxycarbonylalkyl or chloroalkyl group at position 1 proceeded by using an appropriate base or heating to give the corresponding pyrrolo- or pyrido [1,2a] quinazolinones (27,28,29,31,and 32).

• 社団法人日本薬学会の論文
• 1983-07-25

著者

• 大稲 豊生

  Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.

• 山田 義久

  Research Laboratory Of Applied Biochemistry Tanabe Seiyaku Co. Ltd.

• 尾崎 建一

  Research Laboratory Of Applied Biochemistry Tanabe Seiyaku Co. Ltd.

• 大稲 豊生

  Research Laboratory Of Applied Biochemistry Tanabe Seiyaku Co. Ltd.

関連論文

• The Synthesis of Chromone-3-carboxanilides
• Quinazolin-2-ones Having a Spirohydantoin Ring. III. A General and Efficient Synthesis of 3'-Substituted Spiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2', 5(3'H)-triones
• Quinazolin-2ones Having a Spirohydantoin Ring. II. Synthesis of Several Spiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2', 5(3'H)-triones via 5-Hydroxyhydantoin Derivatives
• Quinazolin-2-ones Having a Spirohydantoin Ring.I. : Synthesis of Spiro[1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine]-2,2', 5'-trione by Reaction of 1-Carbamoylisatin with Uera or Guanidine
• Studies on 4 (1H)-Quinazolinones. IV. Convenient Syntheses of 12-Methyl-6H-isoquino [2,1-a] quinazolin-6-one and 6-Methyl-13H-quinazolino [3,4-a] quinazolin-13-one
• Studies on 4 (1H)-Quinazolinones. III. Some Derivatizations of 2-Ethoxycarbonylalkyl-1-substituted-4 (1H)-quinazolinones
• Studies on 4(1H)-Quinazolinones. I. A Convenient Synthesis and Some Reactions of 1-Phenyl-2-substituted-4(1H)-quinazolinones
• Synthesis of the Metabolites of Afloqualone and Related Compounds
• Studies on biologically Active Halogenated Compounds. II. Chemical Modifications of 6-Amino-2-fluoromethyl-3-(o-tolyl)-4 (3H)-quinazolinone and the CNS Depressant Activities of Related Compounds
• 4-Oxo-1,2,3,4-tetrahydroquinazoline. IV. Reactions of 2-Chloromethyl-3-aryl-4-oxo-1,2,3,4-tetrahydroquinazolines
• Studies on Benzoisogranatanine Derivatives. II. Synthesis of 1-Phenethyl-2,4-propano-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines.
• Alkylsulfonyltoluene Derivatives (Diuretics. II.).
• Alkylsulfonyltoluene Derivatives (Diuretics. I.).
• Benzoisogranatanine Derivatives. I. Synthesis of 2'-Hydroxy-5-alkyl-6,7-benzoisogranatanines.

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