Acidic Properties of Benzimidazoles and Substituent Effects. II. The Substituent Effect on the Imidazole Formation from p-Substituted-o-phenylenediamines and on the Acid Dissociation of the Benzimidazoles

スポンサーリンク

概要

• 論文の詳細を見る

• 2-(2-Pyridyl) benzimidazole and 5 (or 6)-substituted derivatives were synthesized by the condensation of p-substituted-o-phenylene diamines with α-picoline in the presence of sulfur or with picolinic acid. These acid dissociation constants were measured in aqueous buffers at 20°by spectrophotometry and fitted the Hammett equation with the use of σ_<para> (ρ=1.3). On the other hand, 2-(2-pyridyl) benzimidazole was nitrated to give its mono-nitro compound which was identical with 5 (or 6)-nitro-2-(2-pyridyl) benzimidazole obtained from p-nitro-o-phenylene diamine. The correlation of the position of substituent groups with their effects for the acidity of 2-(2-pyridyl) benzimidazoles was discussed.

• 社団法人日本薬学会の論文
• 1977-02-25

著者

• 市川 正孝

  福山大学薬学部

• 市川 正孝

  Faculty Of Pharmaceutical Sciences Kumamoto Univerisity

• 久野 拓造

  Faculty Of Pharmaceutical Sciences Kumamoto University

• 久野 拓三

  熊本大学薬学部

関連論文

• 抗腫瘍性ラベンダマイシンの合成研究 : デメチルラベンダマイシンメチルエステルの合成(発表論文抄録(1983年))
• クマリン誘導体の合成研究(第25報) : 4-Methyl-6-acetyl-7-hydroxycoumarinおよび4-Methyl-7-hydroxy-8-acetylcoumarinのニトロ誘導体の合成
• Studies on Organosulfur Compounds. XII. Syntheses and Pharmacological Activities of 2-Heterocyclic Substituted 4(3H)-Quinazolinones
• 有機硫黄化合物の合成化学的研究(第5報) : Benzothiazole誘導体と有機過酸との反応
• 有機硫黄化合物の合成化学的研究(第1報) : 硫黄の存在下, 活性メチル基のo-置換二官能分子との反応
• 抗黴剤の合成化学的研究(第14報) : 硫黄の存在下におけるアニリンと2-ピコリン-1-オキシドとの反応
• 3,4-ジフェニル-5-ニトロフリルチアゾール類及び関連化合物の突然変異性に関する研究(発表論文抄録(1984年),福山大学開学10周年記念号)
• Synthesis of Benzoxazoles, Benzothiazoles and Benzimidazoles and Evaluation of Their Antifungal, Insecticidal and Herbicidal Activities
• フェニルピリジンカルボキサミジン類の合成と抗炎症作用の検索(発表論文抄録(1983年))
• Synthesis and Antiinflammatory Activity of N^1-(Substituted phenyl) pyridinecarboxamidines
• Reaction of Aromatic N-Oxides with Dipolarophiles. V. 1,3-Cycloaddition of 2-Substituted Pyridine N-Oxides with Phenyl Isocyanates
• Synthesis of Benzoxazoles, Benzothiazoles and Benzimidazoles and Evaluation of Their Antifungal, Insecticidal and Herbicidal Activities
• アルコキシフェニルピリジンカルボキサミジン誘導体の合成法の開発
• Reaction of Aromatic N-Oxides with Dipolarophiles. IV. Factors affecting the 1,3-Cycloaddition of Pyridine 1-Oxide with Phenyl Isocyanates
• Acidic Properties of Benzimidazoles and Substituent Effects. V. Protection of Benzimidazoles by N-Alkyl Bond Formation using Vinylpyridines
• 2-位異項環置換-4(3H)-quinazolinone類と求電子試薬との反応
• Reaction of Aromatic N-Oxides with Dipolarophiles. III. Cycloadditions of Substituted Phenyl Isocyanates to 3,5-Dimethyl and 3,5-Dibromopyridine N-Oxides and X-Ray Crystal Structures of the Isomeric Cycloadducts
• Acidic Properties of Benzimidazoles and Substituent Effects. IV. Relationship between the Acidities of N'-(Substituted Phenyl) arylamidines and Ring Closures to Imidazole
• 2-位異項環置換-4(3H)-quinazolinone類と有機過酸との反応
• 有機硫黄化合物の合成化学的研究(第16報) : 4(3H)-Quinazolinone環形成反応におけるアントラニル酸の脱炭酸現象について
• Acidic Properties of Benzimidazoles and Substituent Effects. II. The Substituent Effect on the Imidazole Formation from p-Substituted-o-phenylenediamines and on the Acid Dissociation of the Benzimidazoles
• Studies on Organosulfur Compounds. XIV. Sulfurations and Oxidations of 2,3-Disubstituted 4 (3H)-Quinazolinones
• Studies on Organosulfur Compounds. XIII. The Substituent Effect on the Acid Dissociation of Thioanilides and on the Rate of Oxidation by Hydrogen Peroxide
• 有機硫黄化合物の合成化学的研究(第15報) : 2-(2-Pyridyl)-3-substituted-phenyl-4(3H)-quinazolinone環化反応における置換基の影響
• Studies on Organosulfur Compounds. XI. Selective Cyclization to Benzothiazole by the Reaction between Quinaldine and meta-Substituted Anilines (or Nitro Compounds) under the Modified Willgerodt-Kindler Reaction
• Acidic Properties of Benzimidazoles and Substituents Effects. I. Correlation between Acid Dissociations and Hydrogen Bondings of Some Benzimidazoles
• Syntheses and Pharmacological Activities of 2-Heterocyclic Substituted 4(3H)-Quinazolinone Derivatives
• ニトロフラン誘導体及び関連化合物の抗菌性,突然変異性,発がん性に関する比較試験(発表論文抄録(1984年),福山大学開学10周年記念号)
• ケンフェロールの簡便な合成法の開発
• Carcinogenicity of 2-(2-Furyl)-3-(5-nitro-2-furyl)acrylamide(Af-2)Fed to Female Sprague-Dawley Rats
• Cycloaddition Behavior of Cyclopentadienone toward Allylic Alcohols.Formation of Hydrophthalide Derivatives via Internal Addition of Alcohol Group to Bridged Carbonyl of exo [4+2]π Cycloadducts
• Hetero Diels-Alder Reaction of N-Acyl Imines. I.The Reaction of N'-Thiobenzoyl-N, N-dimethylformamidine with Electron-Deficient Dienophiles. Stereochemical and Mechanistic Aspects
• Phenol-Catalyzed Thione-Thiol Rearrangement of Xanthates and Modified Intermediate Neglect of Differential Overlap (MINDO/3) Analysis of the Reaction Mechanism
• Coupling Reaction of 2-Hydroxyindoline with Arenes by BF_3・Et_2O. A Convenient Synthetic Method of Isolable Diastereomeric Atropisomers
• Thione-Thiol Rearrangement of Xanthates catalyzed by Pyridine N-Oxides. Remarkably Enhanced Reactivity of 4-Dialkylaminopyridine N-Oxides
• Linear Correlation of the Solvolysis Rates of Xanthates with the Grunwald-Winstein Y Values
• Reaction of Aromatic N-Oxides with Dipolarophiles. XVI. Cycloaddition Behavior of Aromatic N-Oxides toward Electron-Deficient Allenes and X-Ray Structure of the 1,4-Dipolar Cycloadduct
• Reaction of Aromatic N-Oxides with Dipolarophiles. XV. Formation of the 1,5-Sigmatropy Products and Their Double Ene Reaction Products
• Catalytic Behavior of Phenols in Pyrolytic Conversion of Allylic Dithiolcarbonates to Allylic Sulfides
• Pericyclic Reactions of 2-Pyrones with Nonconjugated Dienes. Conformational Analysis of the Double Diels-Alder Adducts by Molecular Mechanics Calculation
• Stereoselective Formation of Allylic Sulfides via Two Sequential[3,3]-Sigmatropic Rearrangements of Allylic Xanthates and Its Mechanistic Aspects
• Reaction of Aromatic N-Oxides with Dipolarophiles. XIV. : Inverse-Type Cycloaddition of Pyridine N-Oxides with 1,4-Epoxy-1,4-dihydronaphthalene and Its Mechanistic Aspects
• Reaction of Aromatic N-Oxides with Dipolarophiles. XIII. : Cycloaddition Behavior of Some Nitrones toward N-Phenylmaleimide and Conformation Isomers of the Cycloadducts
• Catalytic Rearrangement of O, S-Dialkyl Dithiocarbonates to S, S-Dialkyl Dithiocarbonates by Pyridine N-Oxides.The Reaction Mechanism
• Pericyclic Reaction of Cyclopentadienones with Nonconjugated Dienes. Formation of Double Diels-Alder Adducts
• Solvolytic Behavior of O-(1-Cyclopropylethyl) S-Methyl Dithiocarbonate and Related Compounds(Organic,Chemical)
• Reaction of Aromatic N-Oxides with Dipolarophiles. XII. : Stereoselective exo Cycloaddition of 3,5-Lutidine N-Oxide with N-Substituted Maleimides and a Frontier Molecular Orbital and Mechanistic Study(Organic,Chemical)
• Reaction of Aromatic N-Oxides with Dipolarophiles. XI. : 1,3-Dipolar Cycloaddition Reaction of Pyridine N-Oxides with Tosyl Isocyanate and One-Pot Synthesis of 2-Oxooxazolo-[4,5-b]pyridine Derivatives
• Reaction of Aromatic N-Oxides with Dipolarophiles. X. : Role of Charge-Transfer Complexes in 1,3-Dipolar Cycloaddition of Pyridine N-Oxides to Phenyl Isocyanate
• Reaction of Aromatic N-Oxides with Dipolarophiles. I. Reaction Products of 3-Picoline 1-Oxide with Phenyl Isocyanate
• 日本薬学会教育賞紹介 加瀬佳年氏
• Reaction of Aromatic N-Oxides with Dipolarophiles. IX. : Formation of 1 : 2 Cycloadduct of 2-Alkylpyridine N-Oxides and Phenyl Isocyanates and a Frontier Molecular Orbital Study
• Reaction of Aromatic N-Oxides with Dipolarophiles. VIII. Carbamation Products of 2-Anilinopyridine Derivatives
• Reaction of Aromatic N-Oxides with Dipolarophiles. VII. Effect of Aromaticity on 1,3-Dipolar Cycloaddition Reactivity of Substituted Pyridine N-Oxides and Preparation of Oxazolo [4,5-b] pyridine Derivatives
• Reaction of Aromatic N-Oxides with Dipolarophiles. VI. Further Studies on the 1,3-Dipolar Cycloaddition Reaction of Pyridine N-Oxides with Phenyl Isocyanates
• 1,3-DIPOLAR CYCLOADDITION OF AROMATIC N-OXIDES TO N-PHENYLMALEIMIDES. STEREOSELECTIVE CYCLOADDITION AND ITS KINETIC AND MECHANISTIC ASPECTS
• クマリン誘導体の合成研究(第21報) : 3-Coumarinacetamideおよび3,4-Dihydro-2-oxo-2H-benzopyran-3-carboxamide誘導体の合成
• Studies on Synthesis of Coumarin Derivatives. XXIV. Nitration of 4,7-Dihydroxycoumarin
• Studies on Synthesis of Coumarin Derivatives. XXII. On the Preparation of N-Pyridyl-2-alkyl-8-oxo-8H-pyrano [3,2-g] benzoxazole-7-carboxamide Derivatives
• Studies on Organosulfur Compounds. X. Dechlorination during 4 (3H) -Quinazolinone Cyclization Process
• Synthesis of Organosulfur Compounds. VIII. Cyclization Products from the Modified Willgerodt-Kindler Reaction
• Synthetic Studies on Fungicidal Agent. IX. Reaction of Quinaldine and Aromatic Primary Amines in the Presence of Sulfur
• Synthetic Studies on Antituberculous Agent. VIII. Reaction between 4-Picoline and Aromatic Primary Amines in the Presence of Sulfur.
• Synthetic Studies on Fungicidal Agent. VII. Reaction of 2-Picoline and Aromatic Primary Amines (or Aromatic Nitro Compounds) in the Presence of Sulfur.
• Studies on Synthesis of Coumarin Derivatives. XXIII. Synthesis and Antibacterial Activity of Derivatives of 3-Substituted-7-amino-4-hydroxy-coumarin
• Studies on Synthesis of Coumarin Derivatives. XX. Synthesis and Antibacterial Activity of Derivatives of N-Substituted 3-Coumarincarboxamide
• クマリン誘導体の合成研究(第17報) : 4-Hydroxy-3-sulfanilamidocoumarin誘導体の合成
• Studies on Synthesis of Coumarin Derivatives. XIX. On te Preparation of (2-Methyloxazolo) coumarin-3-carboxylic Acid Derivatives
• Studies on Synthesis of Coumarin Derivatives. XVIII. Condensation of Ethyl (2-Methyloxazolo) coumarin-3-carboxylates with Aldehyde Groups
• Studies on Synthesis of Coumarin Derivatives. XVI. On the Preparation of N-Substituted-pyranobenzoxazole-carboxamides
• Studies on Synthesis of Coumarin Derivatives. XV. On the Preparation of Ethyl Pyranobenzoxazole-carboxylates.
• Catalytic Rearrangement of O-Cholesteryl S-Alkyl Dithiocarbonates to S-Alkyl S-Cholesteryl Dithiocarbonates by Phenols
• Reaction of Aromatic N-Oxides with Dipolarophiles. II. Reaction of β-Alkylpyridine N-Oxides with Phenyl Isocyanate
• 選考対象, 評価基準の再検討を(日本薬学会学会賞について)
• 有機硫黄化合物の合成化学的研究(第7報) : 硫黄の存在下, 活性メチル, アミンおよびアントラニール酸による4(3H)-Quinazolinone Cyclization
• 有機硫黄化合物の合成化学的研究(第9報)Willgerodt-Kindler反応条件下における4-ピコリンとmeta-置換アニリン類とからの選択的ペンゾチアゾール閉環体について
• Studies on Organosulfur Compounds. IV. Relative Strengths of 2-(2-Pyridyl)-3-phenyl-4 (3H)-quinazolinone Series as Proton Acceptor in Hydrogen Bonding
• Synthesis of Organosulfur Compounds. III. Application of Thiopicolinanilide Series for the Niementowski Synthesis
• 有機硫黄化合物の合成化学的研究(第6報) : N-Substituted-2-(2-pyridyl)-benzimidazole類の合成
• 有機硫黄化合物の合成化学的研究(第2報) : 2-Thiopicolinanilide誘導体のBifunctional化合物に対する反応性

もっと見る 閉じる

スポンサーリンク