Studies on Pyrazolo [3,4-d] pyrimidine Derivatives. IV. On 1-Methyl-and 1-Phenyl-1H-pyrazolo [3,4-d] pyrimidine 5-Oxide

スポンサーリンク

概要

• 論文の詳細を見る

• Various reactions usually carried out on heterocyclic N-oxides were examined on 1-methyl-(IIm-0) and 1-phenyl-1H-pyrazolo [3,4-d] pyrimidine 5-oxide (IIp-0) prepared from the condensation-cyclization of 1-methyl-(IIIm-1) or 1-phenyl-5-amino-4-hydroxyiminomethyl-1H-pyrazole (IIIp-1) and ethyl orthoformate. The reaction of IIp-0 with alkaline solution gave the ring fission product between the 5- and 6-position such as 5-formamido- (IIIp-5) and 5-amino-4-hydroxyiminomethyl-1-phenyl-1H-pyrazole (IIIp-1). Application of the Reissert reaction to II-0 resulted in the formation of the ring fission products such as O-benzoyl derivative of IIIp-1 (IIIp-6) and 5-amino-1-methyl-1H-pyrazole-4-carbonitrile (IIIm-3). Acetic anhydride and IIm-0 gave 1-methyl-1H-pyrazolo [3,4-d] pyrimidin-4-ol-(Im-4). But the reaction with IIp-0 gave both 1-phenyl-1H-pyrazolo [3,4-d] pyrimidine-4-ol (Ip-4) and 5-acetamido-1-phenyl-1H-pyrazole-4-carbonitrile (IIIp-8). Ip-4 was also obtained from the reaction of IIp-0 with tosyl chloride. The thermal decomposition of II-0 afforded 4,4'-bis [1-methyl-1H-pyrazolo [3,4-d] pyrimidine] (IXm) and 4,4'-bis [1-phenyl-1H-pyrazolo [3,4-d] pyrinidime] (IXp) together with 1-methyl-(Im-0) and 1-phenyl-1H-pyrazolo [3,4-d] pyrimidine (Ip-0). The Grignard reaction of II-0 gave 1-Methyl-(IIm-7-9) and 1-phenyl-4-alkyl-1H-pyrazolo-[3,4-d] pyrimidine 5-oxide (IIp-5-9). Im-0 and II-0 were transformed into 1-methyl-(XIXm) and 1-phenyl-1H-pyrazolo [3,4-b] pyridines (XIXp) by the reaction with some active methylene compounds or ketone such as malononitrile (A-1), ethyl cyanoacetate (A-2), ethyl acetoacetate (A-3), acetylacetone (A-4) and cyclohexanone (A-5). Thus, in the presence of ethoxide ion Im-0 reacted with A-1 to give 6-amino-1-methyl-1H-pyrazolo [3,4-d] pyridine-5-carbonitrile (XIXm-1). The direct reaction of IIm-0 with A-1 and A-2 gave 4,5-dihydro-5-hydroxy-1-methyl-1H-pyrazolo [3,4-d] pyrimidine-4-malononitrile (XXm) and ethyl α-cyano-4,5-dihydro-5-hydroxy-1-methyl-1H-pyrazolo [3,4-d] pyrimidine-4-acetate (XXm-2). But the direct reaction with A-3,4 and 5 afforded the corresponding XIXm (XIXm-3,4,and 5), respectively. The reaction of IIp-0 with A-1,3,and 4 formed the corresponding XIXp (XIXp-1,3,and 4) together with IXp (in the case of A-3 and 4), Ip-0 (in the case of A-4) and the ring fission product such as ethyl 2-(4-cyano-1-phenyl-1H-pyrazol-5-ylaminomethylene)-3-oxobutyrate (XXIp-3) and ethyl 2-(4-hydroxy-iminomethyl-1-phenyl-1H-pyrazol-5-ylaminomethylene)-3-oxobutyrate (XXIp-3') (in the case of (A-3).

• 公益社団法人日本薬学会の論文
• 1976-12-25

著者

• 林 英作

  Shizuoka College of Pharmacy

• 東野 武郎

  Shizuoka College of Pharmacy

• 岩井 義久

  Shizuoka College Of Pharmacy

関連論文

• 含窒素芳香族複素環化合物84種の抗腫瘍性について
• 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)
• 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
• 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
• 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
• Pyrazolo[3,4-d]pyrimidine誘導体に関する研究(第3報)1-Methyl-および1-Phenyl-4-chloro-1H-pyrazolo[3,4-d]pyrimidineとCarbanionとの反応
• Pyrazolo[3,4-d]pyrimidine誘導体に関する研究(第2報)4-Chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidineとKetone Carbanionとの反応
• Pyrazolo[3,4-d]pyrimidine誘導体に関する研究(第1報)1-Methyl-および1-Phenyl-1H-pyrazolo[3,4-d]pyrimidineとGrignard試薬との反応

もっと見る 閉じる

スポンサーリンク