Phthalazines. XV. Ring Transformation of Phthalazines into Naphthalenes by Means of Inverse-Electron-Demand Diels-Alder Reaction

スポンサーリンク

概要

• 論文の詳細を見る

• The 1-substituted phthalazines 6 underwent inverse-electron-demand Diels-Alder reaction with the enamines 3 and ynamines 9,resulting in the formation of 1-substituted naphthalenes.Thus, 1-phthalazinecarbonitrile (6b) reacted with 3a-i to give the corresponding 1-naphthonitriles 7a-e, g, h and 2,3-kihydro-1-naphthonitriles 8f, i, respectively. Similarly, reaction of 1-(methylsulfonyl)phthalazine (6c) with 3a, b, d, f gave the corresponding 1-(methylsulfonyl)naphthalenes 10a, b, d and 1-(methylsulfonyl)-2,3-dihydronaphthalene 11f. Furthermore, 1-methylthio- (6e), 1-phenyl- (6f), 1-methyl-(6b), 1-chlorophthalazines (6h) and phthalazine (6a) reacted with 3a to afford the corresponding 4-substituted 2,3-dihydro-1H-benz[f]indenes 12e-h, a, respectively.A similar ring transformation was found to proceed between 1,4-phthalazinedicarbonitrile (14) and 1-methyl-1H-indole (13), giving the benzo[b]carbazoledicarbonitrile (15).Compounds 6b and 6c also underwent inverse-electron-demand Diels-Alder reaction with the ynamines 9a, b to give the corresponding 1-cyano-16a, b and 1-(methylsulfonyl)naphthalenes 17a, b, respectively.

• 社団法人日本薬学会の論文
• 1990-12-25

著者

• 東野 武郎

  School Of Pharmaceutical Sciences University Of Shizuoka

• 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

• 岩本 憲人

  School of Pharmaceutical Sciences, University of Shizuoka

• 宮下 晶

  School of Pharmaceutical Sciences, University of Shizuoka

• 大石 悦男

  School of Pharmaceutical Sciences, University of Shizuoka

• 泰道 直方

  Central Research Laboratories, S S Pharmaceutical Co., Led.,

• 宮下 晶

  School Of Pharmaceutical Sciences University Of Shizuoka

• 岩本 憲人

  静岡県立大学薬学部

• 泰道 直方

  Central Research Laboratories S S Pharmaceutical Co.

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
• Triazolo[4,5-d]pyrimidines. XI. Halogen-Metal Exchange Reaction of 5-Halo-3H-1,2,3-triazolo-[4,5-d]pyrimidines with Butyllithium
• Triazolo[4,5-d]pyrimidines. X. Halogen-Metal Exchange Reaction of 7-Halo-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidines with Butyllithium
• 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
• Gel Filtration of Solubilized Systems. VII. Temperature Effect on the Solubilization of Ethylparaben in Hexaoxyethylene Lauryl Ether Micelles
• Catalytic Action of Azolium Salts. IV. Preparations of 4-Aroylquinazolines and 4-Aroyl-1H-pyrazolo[3,4-d]pyrimidines by Catalytic Action of 1,3-Dimethylimidazolium Iodide
• Catalytic Action of Azolium Salts. III. Aroylation of N-Phenylbenzimidoyl Chlorides with Aromatic Aldehydes in the Presence of 1,3-Dimethylimidazolium Iodide
• 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
• SYNTHESIS OF 2,6-DISUBSTITUTED PYRIDINES BY LITHIATION OF PYRAZOLO[1,5-a]PYRIDINES
• 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
• Purines. X. Reactivities of Methyl Groups on 9-Phenylpurines : Condensation with an Aldehyde or an Ester, and Oxidation with Selenium Dioxide
• Triazole[4,5-d]pyrimidines. IX. Reactions of 5-Chloro- and 5-(Methylsulfonyl)-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidines with C-Nuclephiles
• Purines. VII. : Hydration and Methoxylation of Alkynyl-9H-purines
• Reactions of 3-Benzoyl-3,4-dihydro-2-methyl-4-quinazolinecarbonitrile(2-Methylquinazoline Reissert Compound) with Acid, Base, Sodium Hydride, and Electrophiles
• Purines. VI. Reactions of 2-Chloro- and 2-(Methylsulfonyl)-9-phenyl-9H-purines with Nucleophiles(Organic,Chemical)
• STUDIES ON METHYLGLYOXAL 1. FLUOROMETRIC DETERMINATION OF METHYLGLYOXAL USING HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY
• Ring Transformation of Condensed Pyrimidines by Enamines and Ynamines. Formation of Condensed Pyridines and Condensed Diazocines
• 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)
• P2-101 水道水中の変異原物質MXの付加体形成に関する研究(環境変異原)
• ケテン化学の新展開:α-オキソケテンの合成と反応
• Catalytic Action of Azolium Salts. VI. Preparation of Benzoins and Acyloins by Condensation of Aldehydes Catalyzed by Azolium Salts
• FORMATION OF DEOXYBENZOINS FROM 1,3-DIMETHYL-2-(α-BENZYLOXYBENZYL)BENZIMIDAZOLIUM IODIDES THROUGH REARRANGEMENT FOLLOWED BY EXPULSION OF AZOLIUM YLIDE
• Reaction of 2-Quinolyl Thiocyanate with C-Nucleophiles
• Quinoxalines. XXVII. The Cyanation of 2-Substituted Quinoxaline 4-Oxides with Trimethylsilyl Cyanide
• 水道水中の強力な変異原物質 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) の分布と毒性
• 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.

もっと見る 閉じる

スポンサーリンク