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

スポンサーリンク

概要

• 論文の詳細を見る

• The reaction of N'-thiobenzoyl -N, N-dimethylformamidine (I) with electron-dificient dienophiles was investigated.The reaction of I with N-substituted maleimides (II) afforded exo and endo 1 : 1 cycloadducts (III). The stereochemistry was determined by analysis of ^1H-nuclear magnetic resonance (^1H-NMR) spectral data based on the modified neglect of diatomic overlap (MNDO) optimized structures. An equilibrium was observed between the starting materials (I and II) and 1 : 1 cycloadducts (III). The reaction of I with II in the presence of acetic acid afforded thiazine derivatives(IV), through elimination of dimethylamine from the primary cycloadduct (III). The reactions of I with several electron-deficient dienophiles were also examined. The reaction behavior is discussed in terms of frontier molecular orbital (FMO) theory and kinetic factors.

• 公益社団法人日本薬学会の論文
• 1993-01-15

著者

• 松岡 俊和

  Faculty Of Pharmaceutical Sciences Kumamoto University

• 原野 一誠

  Faculty of Pharmaceutical Sciences, Kumamoto University

• 久野 拓造

  Faculty Of Pharmaceutical Sciences Kumamoto University

• 原野 一誠

  熊本大学 薬

• 原野 一誠

  熊本大学薬学部

• 久野 拓三

  熊本大学薬学部

• 上村 敏啓

  Faculty of Pharmaceutical Sciences, Kumamoto University

• 上村 敏啓

  Faculty Of Pharmaceutical Sciences Kumamoto University

関連論文

• 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
• The X-Ray Analysis of Caesalpin J from Sappan Lignum
• 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
• THE ROLE OF THROUGH-BOND INTERACTION IN THERMAL BEHAVIOR OF CAGE MOLECULES
• 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
• Catalytic Rearrangement of O, S-Dialkyl Dithiocarbonates to S, S-Dialkyl Dithiocarbonates. IV. Use of Boron Trifluoride Etherate as Catalyst
• Rearrangement and trans-Elimination contrary to the Chugaev Reaction Rule. XIII. Solvent Effect on Rearrangement Reaction of Allylic Xanthates and a Correction of the Former Report
• Catalytic Rearrangement of Xanthates to Dithiolcarbonates
• Rearrangement and trans-Elimination contrary to the Chugaev Reaction Rule. IX. Thermal Rearrangement of 2-Cycloalkenyl S-Alkyl Xanthate
• Rearrangement and trans-Elimination contrary to the Chugaev Reaction Rule. VIII. Thermal Rearrangement of 2-Alkenyl S-Alkyl Xanthate
• Reaction of Aromatic N-Oxides with Dipolarophiles. I. Reaction Products of 3-Picoline 1-Oxide with Phenyl Isocyanate
• 3-Methyl-10-thiaisoalloxazineの新しいプロペラ型付加物
• 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
• 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 Antitumor Substances. III. Syntheses of Bis(methanesulphonylthio)alkanes
• 薬学領域の情報化への対応と問題点:熊大薬学部の取り組み (特集 平成9年度日本薬学図書館協議会研究集会 テーマ:学内LANと図書館)
• 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