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
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概要
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Two novel ring systems, 12-methyl-6H-isoquino [2,1-a] quinazolin-6-one (2) and 6-methyl-13H-quinazolino [3,4-a] quinazolin-13-one (3a), were synthesized. Reaction of 3-methylisocoumarin (4) with 2-cyanoaniline gave 2-(2-cyanophenyl)-3-methylisocarbostyril (5), which was converted to 2-(2-carbamoylphenyl)-3-methylisocarbostyril (6) by treatment with alkaline hydrogen peroxide. The cyclization of 6 with boron trifluoride etherate afforded 2. Compound 3a was prepared by the reaction of 2-methyl-4H-3,1-benzoxazin-4-one (8a) with 2-cyanoaniline in one step. Some derivatives (3b-g) were also prepared by this method. The reaction mechanism is discussed.
- 社団法人日本薬学会の論文
- 1984-06-25
著者
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大稲 豊生
Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.
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山田 義久
Research Laboratory Of Applied Biochemistry Tanabe Seiyaku Co. Ltd.
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尾崎 建一
Research Laboratory Of Applied Biochemistry Tanabe Seiyaku Co. Ltd.
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大稲 豊生
Research Laboratory Of Applied Biochemistry Tanabe Seiyaku Co. Ltd.
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- 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.).
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