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

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概要

• 論文の詳細を見る

• Acid hydrolysis of the 6-methylpyrazolopyrimidine Reissert compound (6) gave the ring-opened product (12) and the oxazole (13). Alkaline hydrolysis of 6 afforded the 6-methylpyrazolopyrimidine (7) and benzoic acid (15). The anion (1) of 6 mainly underwent both aromatization and rearrangement, resulting in the formation of the 6-methylpyrazolopyrimidinecarbonitrile (20) and the 4-benzoyl-6-methylpyrazolopyrimidine (21) together with by-products such as 7,the dimer (22), the benzoate (23a), and O-benzoylbenzoin (24a). The anion I added to the carbonyl carbon of aromatic aldehydes (8a-c), giving the benzoates (23a-c) together with 7,the O-benzoylaroins (24a-c), and the O-benzoylcyanohydrins (27a, c).

• 社団法人日本薬学会の論文
• 1990-01-25

著者

• 東野 武郎

  School Of Pharmaceutical Sciences University Of Shizuoka

• 丹治 健一

  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

• 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.,

• 佐藤 進

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

• 宮下 晶

  School Of Pharmaceutical Sciences University Of Shizuoka

• 佐藤 進

  Department Of Pharmacology Pharmaceutical Institute Tohoku University

• 丹治 健一

  School Of Food & Nutritional Sciences University Of Shizuoka

• 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
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• 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
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• 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
• Effects of Atrial Natriuretic Peptide on Angiotensin II-Induced Antinatriuresis in Anesthetized Dogs
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• 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
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• 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
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• Purines. VI. Reactions of 2-Chloro- and 2-(Methylsulfonyl)-9-phenyl-9H-purines with Nucleophiles(Organic,Chemical)
• Quinoxalines. XXII. Aryl Migration of 2-Aroylquinoxalines to 2-Arylquinoxalines
• Studies on Pyrimidine Derivatives. XXXIII. Synthesis of Alkyl Pyrimidinyl Ketones by Means of Nitrosation of Alkylpyrimidines
• Studies on Pyrimidine Derivatives. XXVII. Synthesis of 2- and 4-Pyrimidinyl Ketones by Means of the Hydration of Alkynylpyrimidines
• Studies on Pyrimidine Derivatives. XXVI. Synthesis of Derivatives containing a 1,3-Dicarbonyl Side Chain
• STUDIES ON METHYLGLYOXAL 1. FLUOROMETRIC DETERMINATION OF METHYLGLYOXAL USING HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY
• Studies on Pyrimidine Derivatives. XXV. Reaction of Pyrimidinyl Aldehydes and Ketones with Witting Reagents
• Studies on Pyrimidine Derivatives. XX. Synthetic Utility of Hydroxymethylpyrimidines and Related Compounds
• ピリミジン誘導体の研究(第11報)Ethoxycarbonylacetamidineとβ-ジカルボニル化合物との反応
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• 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)
• Studies on Pyrazolo[3,4-d]pyrimidine Derivatives. XIV. : Preparation and Reactions of 1-Phenyl-1H-pyrazolo-[3,4-d]pyrimidine Reissert Compound
• Studies on Organic Fluorine Compounds. VII. Trifluoromethylation of Aromatic Compounds
• 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
• The Adrenergic Neurone Blocking Action of [2-(Methylphenylamino)ethyl]guanidine Sulfate.I
• The Adrenergic Neurone Blocking Action of [2-(Methylphenylamino)-ethyl] guanidine Sulfate. II.
• 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.

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