Grignard Reactions of 1-Phthalazine-, 2-Ouinoxaline-, and 4-Cinnoline-carbonitrile

スポンサーリンク

概要

• 論文の詳細を見る

• The Grignard reactions of 1-phthalazine-(V-0), 2-quinoxaline (VI-0), and 4-cinnolinecarbonitrile (VII-0) were carried out. Grignard reagent used in this study was as follows ; phenylmagnesium bromide, benzylmagnesium chloride, isopropylmagnesium bromide, ethylmagnesium bromide, and methylmagnesium iodide. When a mixture of V-0 and Grignard reagent in tetrahydrofuran (THF) was refluxed for 3 hr, 1-alkylphthalazine (Va), 4-alkyl-3,4-dihydro-1-phthalazinecarbonitrile (Vc), 4-alkyl-1-phthalazinecarbonitrile (Vc'), 2-alkyl-1(2H)-phthalazinone (Vd), and 4-alkyl-3,4-dihydro-3-(1-phthalazinyl)-1-phthalazinecarbonitrile (Ve) were formed together with 1-benzoylphthalazine (Vb-1), 1,4-diethyl-phthalazine (Vf-4), 1,2-dihydro-1,1,2-triethyl-phthalazine (Vg-4), and 3,4-dimethyl-3,4-dihydro-1-phthalazinecarbonitrile (Vh-5), although the yields of all products were small. The reaction of VI-0 in THF carried out under the same conditions as V-0 gave 2-alkylquinoxaline (VIa), 2-acylquinoxaline (VI-b), 3-alkyl-3,4-dihydro-2-quinoxalinecarbonitrile (VIc), 3-alkyl-2-quinoxalinecarbonitrile (VIc'), and 1-alkyl-2 (1H)-quinoxalinone (VId) together with 2,2' : 3', 2"-terquinoxaline (VIi), in very small yields. The reaction of VII-0 with phenylmagnesium bromide and methylmagnesium iodide in benzene gave only d type of the compound (1-phenyl-(VIId-1), and 1-methyl-4 (1H)-cinnolinone (VIId-5)), and did not isolate other type of the compound. These, a, b, and c type of the compounds were expected reaction products, and other, c', d, e, f, g, and h type of the compounds were unexpected products. Especially, e type of the compound was the product peculiar to the Grignard reaction of V-0,and d type of the compound was characteristic product of the Grignard reactions of the cyanobenzodiazines except 4-quinazolinecarbonitrile (IV-0) giving only a type of the compound. The possible mechanisms of the formations of a, b, c, c', d, and e type of the compounds were proposed.

• 社団法人日本薬学会の論文
• 1977-04-25

著者

• 大石 悦男

  Division Of Environmental Health Sciences Graduate School Of Nutritional & Environmental Science

• 大石 悦男

  Laboratory Of Organic Chemistry Graduate School Of Nutritional And Environmental Sciences University

• 大石 悦男

  Shizuoka College of Pharmacy

• 林 英作

  Shizuoka College of Pharmacy

• 東野 武郎

  Shizuoka College of Pharmacy

• 飯沼 光寿

  Shizuoka College of Pharmacy

• 宇都宮 岩生

  Shizuoka College of Pharmacy

• 飯島 千穂子

  Shizuoka College of Pharmacy

• 飯島 千穂子

  School of Pharmaceutical Sciences, University of Shizuoka

• 飯島 千穂子

  School Of Pharmaceutical Sciences University Of Shizuoka

関連論文

• Mutagenicity of Condensed Pyridazines with Different Substituents
• 含窒素芳香族複素環化合物84種の抗腫瘍性について
• Ring Transformation of Fused Pyridazines. III. 1-Substituted Phthalazines with Ynamines
• New N-N Bond Cleavage of Fused Chloropyridazines with Ynamines
• N-N BOND CLEAVAGE OF 1-CHLOROPHTHALAZINE BY THE REACTION WITH YNAMINES
• Condensed Pyridazines. VIII. Reaction of Diazolopyridazines with Ynamine. Formation of Ben-zodiazoles and Diazolodiazocines
• Phthalazines. XV. Ring Transformation of Phthalazines into Naphthalenes by Means of Inverse-Electron-Demand Diels-Alder Reaction
• Studies on Pyrazolo[3,4-d]pyrimidne Derivatives. XVII. : Reactions of 5-Benzoyl-4,5-dihydro-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4-carbonitrile : The 6-Methylpyrazolopyrimidine Reissert Compound
• Purines. VIII. : Reactions of 1-Benzoyl-1,6-dihydro-9-phenyl-9H-purine-6-carbonitrile (9-Phenylpurine Reissert Compound) with Acid, Bases, and Electrophiles
• 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
• Phthalazine誘導体に関する研究(第13報)1-置換Phthalazine 3-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
• Phthalazine誘導体に関する研究(第11報)1-置換および1,4-ジ置換Phthalazine N-OxideとAcetic AnhydrideおよびAcid Chlorideとの反応
• 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
• Catalytic Action of Azolium Salts. II. Aroylation of 4-Chloroquinazolines with Aromatic Aldehydes Catalyzed by 1,3-Dimethylbenzimidazolium Iodide
• Catalytic Action of Azolium Salts. I. : Aroylation of 4-Chloro-1H-pyrazolo[3,4-d]pyrimidines with Aromatic Aldehydes Catalyzed by 1,3-Dimethylbenzimidazolium Iodide
• Triazolo[4,5-d]pyrimidines. XII. Reaction of 6-Benzoyl-6,7-dihydro-3-phenyl-3H-1,2,3-triazolo-[4,5-d]pyrimidines (Triazolopyrimidine Reissert Compounds) with Acid, Base, and Electrophile
• Quinoxalines. XXII. Aryl Migration of 2-Aroylquinoxalines to 2-Arylquinoxalines
• STUDIES ON METHYLGLYOXAL 1. FLUOROMETRIC DETERMINATION OF METHYLGLYOXAL USING HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY
• 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
• Phthalazine誘導体に関する研究(第2報) : 1-(Methylsulfonyl)-4-phenylphthalazineについて
• 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
• Purines. V. Reaction of 9-Phenyl-9H-purine-6-carbonitrile with Nucleophilic Reagents
• Reaction of 2-Quinolyl Thiocyanate with C-Nucleophiles
• Quinoxalines. XXVII. The Cyanation of 2-Substituted Quinoxaline 4-Oxides with Trimethylsilyl Cyanide
• 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
• Cinnoline誘導体に関する研究(第8報)4-Cinnolinecarbonitrileと活性メチレン化合物との反応について
• Cinnoline誘導体に関する研究(第7報)4-CinnolinecarbonitrileとKetone Carbanionとの反応について
• Quinoxalines.XXXVI. : Reactions of 2-Quinoxalinyl Thiocyanate with Nucleophiles
• Quinoxaline誘導体に関する研究(第25報)2-Nitroquinoxalineの合成とその化学的性質について
• Quinoxaline誘導体に関する研究(第21報) : 2-置換Furo[2,3-b]-quinoxaline, 2-置換Pyrrolo[2,3-b]quinoxalineの合成
• Quinoxaline誘導体に関する研究(第20報)2-Alkoxyquinoxaline誘導体とSodium Amideとの反応について
• Quinoxaline誘導体に関する研究(第14報) : 2-置換-quinoxaline 4-OxideとAcetophenoneとの反応
• Quinoxaline誘導体に関する研究(第11報) : Quinoxaline 1-Oxideについて
• Quinoxaline N-Oxideに関する研究(第7報) : Quinoxaline 1-OxideとPhenyl isocyanateとの反応について
• Quinoxaline N-Oxideに関する研究(第6報) : 2-Phenyl-および2-Alkyl-3-phenylquinoxalineの紫外スペクトルに観察される知見
• Quinoxaline N-Oxideに関する研究(第4報) : 2-Phenylquinoxaline 4-OxideとGrignard化合物との反応について
• 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
• Phthalazine誘導体に関する研究(第7報) : 1-(Methylsulfonyl)-phthalazineと求核試薬との反応について
• 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9報)1-(Methylsulfonyl)phthalazineとケトンとの反応について(補遺)
• Phthalazine誘導体に関する研究(第10報)1-(Methylsulfonyl)-phthalazineとGrignard試薬との反応について
• Phthalazine 誘導体に関する研究(第6報) : 1-Methylおよび1-BenzylphthalazineのN-Oxidationについて
• Phthalazine誘導体に関する研究(第5報) : 1-(Methlsulfonyl)-4-phenyl-phthalazineと活性メチレン化合物との反応について
• Phthalazine誘導体に関する研究(第4報) : 1-Phenylphthalazine 3-OxideとAcetophenoneとの反応について
• Phthalazine誘導体に関する研究(第3報) : 1-(Methylsulfonyl)-4-phenylphthalazineとケトンとの反応について
• 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