Triazolo [4,5-d] pyrimidines. II. On 3-Methyl- and 3-Phenyl-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

• Various reactions of 3-methyl- (Im) and 3-phenyl-3H-1,2,3-triazolo [4,5-d] pyrimidine (Ip) were examined. Im was prepared by cyclization of 5-amino-4-methylaminopyrimidine (II) with nitrous acid, and Ip was prepared by the catalytic reduction of 7-chloro-3-phenyl-3H-1,2,3-triazolo [4,5-d] pyrimidine (IIIp) using palladium on magnesium oxide carrier as a catalyst. In warm alkaline solution Im underwent ring fission to give 5-amino-1-methyl-1H-1,2,3-triazole-4-carboxaldehyde (IVm). In dilute sulfuric acid both Im and Ip underwent ring fission to yield IVm and 5-amino-1-phenyl-1H-1,2,3-triazole-4-carboxaldehyde (IVp), respectively, in good yields. However, the reaction of Im with the methoxide ion resulted in the formation of 7,7'-bis [3-methyl-3H-1,2,3-triazolo [4,5-d] pyrimidine] (Vm) and 3-methyl-7-(5-amino-1-methyl-1H-1,2,3-triazol-4-yl)-3H-1,2,3-triazolo [4,5-d] pyrimidine (VIm), although the yields were poor. Both Im and Ip dimerized in the presence of the cyanide ion to give Vm and 7,7'-bis [3-phenyl-3H-1,2,3-triazolo [4,5-d] pyrimidine] (Vp), respectively, in good yields. N, N-Dimethylaniline (IX) reacted with Im in dulute sulfuric acid to give 5-amino-4-[bis [4-N, N-dimethylaminophenyl] methyl]-1-methyl-1H-1,2,3-triazole (VIIIm) in poor yield. VIIIm was also obtained by condensation of IX and IVm in dilute sulfuric acid.

• 公益社団法人日本薬学会の論文
• 1979-10-25

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

• 香取 達彦

  Central Research Laboratories, SS Pharmaceutical Co., Ltd.

• 香取 達彦

  Central Research Laboratories S S Pharmaceutical Co. Ltd.

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
• Studies on Synthesis of 3-O-Alkyl-D-glucose and 3-O-Alkyl-D-allose Derivatives and Their Biological Activities(Biological)
• Reactions of 3-Benzoyl-3,4-dihydro-2-methyl-4-quinazolinecarbonitrile(2-Methylquinazoline Reissert Compound) with Acid, Base, Sodium Hydride, and Electrophiles
• Quinoxalines. XXII. Aryl Migration of 2-Aroylquinoxalines to 2-Arylquinoxalines
• Studies on Pyrazolo[3,4-d]pyrimidine Derivatives. XVI. Preparation of Reissert Compounds from Condensed Pyrimidine Systems Catalyzed by Lewis Acids(Organic,Chemical)
• Studies on Pyrazolo[3,4-d]pyrimidine Derivatives. XV. Reactions Involving the Formation of the Anion of the Reissert Compound Derived from 1H-Pyrazolo[3,4-d]pyrimidine(Organic,Chemical)
• 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
• ALKYLAMINO MONOSACCHARIDES AS PROMOTERS OF PLANT GROWTH
• 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.
• 麦門冬(中国産)の成分研究(第1報)
• 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.
• Triazolo[4,5-d]pyrimidineに関する研究(第1報)7-Chloro-3-methyl-3H-1,2,3-triazolo[4,5-d]pyrimidineとNucleophileとの反応
• 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