Triazolo [4,5-d] pyrimidines. VIII. Aryl Migration of 7-Aroyl-3H-1,2,3-triazolo [4,5-d] pyrimidines to 7-Aryl-3H-1,2,3-triazolo [4,5-d] pyrimidines

スポンサーリンク

概要

• 論文の詳細を見る

• When mixtures of 7-chloro-3-phenyl-3H-1,2,3-triazolo [4,5-d] pyrimidine (4), aromatic aldehydes (5), and a catalytic amount of 1,3-dimethylbenzimidazolium iodide were refluxed in tetrahydrofuran (THF) in the presence of sodium hydride, 7-aroyl-3-phenyl-3H-1,2,3-triazolo [4,5-d]-pyrimidines (1) were obtained in moderate yields. Although the yield was unsatisfactory, the reaction of 1 with sodium hydroxide in dimethyl sulfoxide (DMSO) resulted in aryl migration, followed by ready oxidative decarboxylation, giving 7-aryl-3-phenyl-3H-1,2,3-triazolo [4,5-d]-pyrimidines (3) by way of 7-aryl-6,7-dihydro-3-phenyl-3H-1,2,3-triazolo [4,5-d] pyrimidine-7-carboxylic acids (2). When the reaction mixture of 1 with sodium hydroxide was directly subjected to potassium ferricyanide oxidation, 1 was easily convertible to 3 in good yield.

• 公益社団法人日本薬学会の論文
• 1985-04-25

著者

• 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

• 宮下 晶

  Shizuoka College of Pharmacy

• 竹元 万寿美

  Shizuoka College of Pharmacy

関連論文

• Condensed Pyridazines. VII. : Reaction of 7-(Methylsulfonyl)-1-phenyl-1H-imidazo[4,5-d]pyridazine with Nucleophiles
• Condensed Pyridazines. VI. Reaction of 7-(Methylsulfonyl)-1-phenyl-1H,2,3-triazolo[4,5-d]pyridazine with Carbanions and Enamines(Organic,Chemical)
• Condensed Pyridazines. V. Reactions of 7-(Methylsulfonyl)-1-phenyl-1H-1,2,3-triazolo[4,5-d]pyridazine with Methoxide Ion, Grignard Reagents, Hydrazines, and Amines(Organic,Chemical)
• 縮合環を有するPyridazine誘導体に関する研究(第4報)7-Methoxy-1-phenyl-1H-pyrazolo[3,4-d]pyridazine 5-Oxideの化学的性質
• 縮合環を有するPyridazine誘導体に関する研究(第3報)4,7-Dichloro-1-phenyl-1H-pyrazolo[3,4-d]pyridazineとCarbanion類との反応
• 縮合環を有するPyridazine誘導体に関する研究(第2報)5-Phenylpyrido-[2,3-d]pyridazine 7-Oxideの化学的性質
• 縮合環を有するPyridazine誘導体に関する研究(第1報)5,8-Dichloropyrido-[2,3-d]pyridazineとCarbanionとの反応
• Phthalazine誘導体に関する研究(第14報)Phthalazine2-OxideとAcetylenic Dienophileとの反応
• 環状ヒドラジド構造を含む複素環化合物の合成とその抗腫瘍性について
• Grignard Reactions of 1-Phthalazine-, 2-Ouinoxaline-, and 4-Cinnoline-carbonitrile
• Transformation of Quinazoline into 2(1H)-Quinolinones with Alkanoic Anhydrides
• Ring Fission of Quinazolines by Means of the Reissert Reaction
• Gel Filtration of Solubilized Systems. VII. Temperature Effect on the Solubilization of Ethylparaben in Hexaoxyethylene Lauryl Ether Micelles
• Quinoxalines. XXII. Aryl Migration of 2-Aroylquinoxalines to 2-Arylquinoxalines
• Studies on Pyrazolo[3,4-d]pyrimidine Derivatives. XIV. : Preparation and Reactions of 1-Phenyl-1H-pyrazolo-[3,4-d]pyrimidine Reissert Compound
• Reactions of the Anion of Quinazoline Reissert Compound (3-Benzoyl-3,4-dihydro-4-quinazolinecarbonitrile) with Electrophiles
• Preparation and Reactions of Quinazoline Reissert Compound (3-Benzoyl-3,4-dihydro-4-quinazolinecarbonitrile)
• A Novel Skeletal Rearrangement of Aromatic N-Oxides upon Electron Impact
• Quinoxaline 誘導体に関する研究(第24報) : 2-Chloroquinoxaline と各種 C-Nucleophile との反応
• Quinoxaline誘導体に関する研究(第23報) : 2-Chloroquinoxalineと各種Nucleophileとの反応
• Triazolo [4,5-d] pyrimidines. VIII. Aryl Migration of 7-Aroyl-3H-1,2,3-triazolo [4,5-d] pyrimidines to 7-Aryl-3H-1,2,3-triazolo [4,5-d] pyrimidines
• Reaction of 4-Aroylquinazolines with Sodium Hydroxide : Aryl Migration to Give 4-Aryl-3,4-dihydro-4-quinazolinecarboxylic Acids and Formation of Quinazoline and Aroic Acids
• Studies on Pyrazolo [3,4-d] pyrimidine Derivatives. XIII. Aryl Migration of 4-Aroyl-1H-pyrazolo [3,4-d] pyrimidines to 4-Aryl-4,5-dihydro-1H-pyrazolo [3,4-d] pyrimidine-4-carboxylic Acids
• 5-Amino-1-phenyl-1H-1,2,3-triazole-4-carbaoxaldehydeおよび関連化合物のDimroth転位
• Purines. V. Reaction of 9-Phenyl-9H-purine-6-carbonitrile with Nucleophilic Reagents
• Studies on the Reaction of π-Deficient Heterocycles with Aromatic Aldehyde in the Presence of Cyanide Ion
• Studies on the Reaction of Quinazoline with Aromatic Aldehyde in the Presence of Cyanide Ion. I. The Extension of the Benzoin Condensation
• Catalytic Reduction of Heterocyclic Aromatic Amine Oxides with Raney Nickel. II. Reduction of 4-Substituted Quinoline 1-Oxide Derivatives.
• Catalytic Reduction of Heterocyclic Aromatic Amine Oxides with Raney Nickel. I. Reduction of 4-Substituted Pyridine 1-Oxide Derivatives.
• A New Deoxygenation Reaction of an Aromatic Heterocyclic N-Oxides
• Catalytic Reduction of Heterocyclic Aromatic Amine N-Oxides with Raney Nickel. IV.^ Reduction of 4,4'-Azopyridine 1,1'-Dioxide, 4,4'-Azoxypyridine 1,1'-Dioxide, and 2-Styrylpyridine 1-Oxide.
• On the Reaction of Quinazoline with Active Methylene Compound
• Catalytic Reduction of Heterocyclic Aromatic Amine Oxides with Raney Nickel. III. Reduction of Hydroxamic Acid-type N-Oxides.
• On N-Oxidation of 4-Alkyl-, 4-Phenyl-quinazoline and Reaction of 4-Methylquinazoline 1-Oxide
• Triazolo [4,5-d] pyrimidines. V. The Nucleophilic Substitution of 7-Chloro- and 7-(p-Tolylsulfonyl)-3-phenyl-3H-1,2,3-triazolo [4,5-d] pyrimidines
• Triazolo [4,5-d] pyrimidines. VI. 3-Phenyl-3H-1,2,3-triazolo [4,5-d]-pyrimidine-7-carbonitrile and Related Compounds
• Triazolo [4,5-d] pyrimidines. IV. The Grignard Reaction of 3-Substituted 3H-1,2,3-Triazolo [4,5-d] pyrimidines
• Triazolo [4,5-d] pyrimidines. III. The Transformation of 3-Substituted 3H-1,2,3-Triazolo [4,5-d] pyrimidines into 3-Substituted 3H-1,2,3-Triazolo [4,5-b] pyridines
• Triazolo [4,5-d] pyrimidines. II. On 3-Methyl- and 3-Phenyl-3H-1,2,3-triazolo [4,5-d] pyrimidines
• The Transformation of 3,4-Dihydro-4-quinazolinylmethyl Alkyl Ketones into Quinolines
• The Transformation of Pyrido [2,3-d] pyrimidine into 1,8-Naphthyridine
• Mass Spectra of 3-Alkyl-4-cinnolinecarbonitriles
• The Mass Spectra of Pyrido [2,3-d] pyrimidines
• Studies on the Reactions of Pyrido[2,3-d]pyrimidine 3-Oxide with Ketones. The Transformation of Pyrido[2,3-d]pyrimidine 3-Oxide into 1,8-Naphthyridines
• Studies on the Reaction of Quinazoline 3-Oxide with Ketone. The Transformation of Quinazoline 3-Oxide into Quinoline Derivatives
• On the Reaction of 4-Quinazolinecabonitrile with Nucleophilic Reagents. IV. Reaction of 4-Quinazolinecarbonitrile with Active Methylene Compounds.
• On the Reaction of 4-Quinazolinecarbonitrile with Nucleophilic Reagents. III. Reaction of 4-Quinazolinecarbonitrile with Ketones.
• On the Reaction of 4-Quinazolinecarbonitrile with Nucleophilic Reagents. II. Reaction of 4-Quinazolinecarbonitrile with Grignard Reagents.
• Studies on Quinazoline 3-Oxide.
• Phthalazine誘導体に関する研究(第1報) : 1-PhenylphthalazineのN-Oxidationおよび1-Phenylphthalazine 3-Oxideの化学的性質について
• Studies on 4-Chloropyrido [2,3-d] pyrimidine and Pyrido [2,3-d] pyrimidine
• On the Reaction of 1-Chloroisoquinoline and 4-Chloroquinazoline with Several Ketone Carbanions
• Studies on Pyrazolo [3,4-d] pyrimidine Derivatives. V. On the Transformation of 1H-Pyrazolo [3,4-d] pyrimidines into 1H-Pyrazolo [3,4-b] pyridines
• Studies on Pyrazolo [3,4-d] pyrimidine Derivatives. IV. On 1-Methyl-and 1-Phenyl-1H-pyrazolo [3,4-d] pyrimidine 5-Oxide

もっと見る 閉じる

スポンサーリンク