4-Oxo-1,2,3,4-tetrahydroquinazoline. IV. Reactions of 2-Chloromethyl-3-aryl-4-oxo-1,2,3,4-tetrahydroquinazolines

スポンサーリンク

概要

• 論文の詳細を見る

• Ring expansion reaction and dehydrochlorination reaction of substituted-2-chloromethyl-3-aryl-4-oxo-1,2,3,4-tetrahydroquinazolines (2a-g) were investigated. The required starting materials 2a-g were prepared from the corresponding 4 (3H) quinazolines (1a-g) by NaBH_4 reduction in excellent yields. 2a-f were easily converted to dehydrochlorination products 3a-f in CHCl_3 at room temperature. On the other hand, treatments of 2a-f with EtONa in EtOH afforded ring expansion products 4a-f. The mechanism of the ring expansion reaction was proved by the isolation of an intermediate, azirinoquinazoline (7). The investigation was extended to the reactions of azirinoquinazoline (7) with nucleophiles. The reactions with NaBH_4,MeOH, AcOH, PhSH, and EtSH proceeded analogously to give benzodiazepines (8,9,10,11,and 12).

• 公益社団法人日本薬学会の論文
• 1974-03-25

著者

• 井上 一三

  Research Laboratories of Tanabe Seiyaku Co., Ltd.

• 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.

• 井上 一三

  Research Laboratories Of Tanabe Seiyaku Co. Ltd.

• 井上 一三

  Department Of Synthetic Chemistry 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

• Studies on Biologically Active Nucleosides and Nucleotides. IV. : Synthesis of 1-β-D-Arabinofuranosyl-2-aralkylamino-1,4-dihydro-4-iminopyrimidine Hydrochlorides
• The Synthesis of Chromone-3-carboxanilides
• 121.ビタミンB_6誘導体の研究(XIII) : ピリドキシル-デヒドロホモシステインチオラクトンの合成(一般研究発表要旨)
• ビタミンB_6誘導体の研究 : (X)ピリドキサールおよびピリドキサールリン酸とホモシステインエステルの結合化合物の合成とその理化学的性質
• 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
• Synthetic Studies on 2-Pyrrolidinone Derivatives. II. The Configuration of Stereoisomers of 1-Phenyl-3-amino-5-methyl-2-pyrrolidinone.
• 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
• Synthesis of 3-Amino-3-(5-fluorouracil-1-yl) propionic Acid and 4-Amino-4-(5-fluorouracil-1-yl) butyric Acid Derivatives
• 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.
• 29.ビタミンB_6誘導体の研究 : (II)PyridoxalおよびPyridoxal phosphateとDL-Homocysteine結合化合物エステル類合成(一般研究発表要旨)
• Synthetic Studies on 2-Pyrrolidinone Derivatives. I. Synthesis of 1-Phenyl-3-dialkylamino-2-pyrrolidinone and its 5-Methyl Analog.

もっと見る 閉じる

スポンサーリンク