Thermal Rearrangements of Cyclic Amine Ylides. VIII. : Intramolecular Cyclization of 2-Ethynylpyridine N-Ylides into Indolizines and Cycl[3.2.2]azines

スポンサーリンク

概要

• 論文の詳細を見る

• Treatment of 6-unsubstituted 2-ethynyl-1-phenacylpyridinium bromides (10a-c) with 1,5-diazabicyclo[5.4.0.]undec-5-ene in refluxing benzene resulted in cyclization to give the 3-benzoyl-indolizines(11) via the N-ylide intermediates 13,whereas heating the salts 10 in refluxing acetic acid afforded the 1-benzoylindolizines (12). Upon similar treatment with the base, 2-ethynyl-6-methylpyridinium salts (20a-c) gave the 3-benzoyl-5-methylindolizines(22); in the case of the phenylacetylene compound 20c, 2,3-diphenylcyc[3.2.2]azine (23) was also obtained. However, the reaction of 6-amino-2-ethynylpyridines (27a-c) with phenacyl bromide produced 5-ethynyl-1-azaindolizines (28), which were converted into 1-azacycl[3.2.2]azines (29). The mechanisms of these intramolecular cyclizations are discussed.

• 公益社団法人日本薬学会の論文
• 1988-10-25

著者

• 土屋 隆

  Faculty of Pharmaceutical Sciences, Hokuriku University

• 土屋 隆

  School of Pharmacy, Hokuriku University

• 指田 春喜

  School of Pharmacy, Hokuriku University

• 指田 春喜

  北陸大学薬学部

• 指田 春喜

  Faculty Of Pharmaceutical Sciences Hokuriku University

• 土屋 隆

  Faculty Of Pharmaceutical Sciences Hokuriku University

• 加藤 昌信

  School of Pharmacy, Hokuriku University

• 加藤 昌信

  School Of Pharmacy Hokuriku University

関連論文

• Studies on Seven-Membered Heterocycles.XXXIII. : Synthesis of Fully Unsaturated 1,2,5-Triazepines by Photochemical Ring Expansion of 4-Azidopyridazines
• SYNTHESIS OF FULLY UNSATURATED MONOCYCLIC 1,2,5-TRIAZEPINES FROM 4-AZIDOPYRIDAZINES
• Studies on Diazepines. XXVIII. Syntheses of 5H-1,3-Diazepines and 2H-1,4-Diazepines from 3-Azidopyridines(Organic,Chemical)
• REGIO-SELECTIVE DIAZEPINE FORMATION FROM 3-AZIDOPYRIDINES : THE FIRST EXAMPLES OF MONOCYCLIC 2H-1,4-DIAZEPINES
• Studies on Diazepines. XXI. Photochemical Synthesis of 1H-2,4-Benzodiazepines from 4-Azidoisoquinolines
• PHOTOLYSIS OF PYRIDYL AZIDES IN THE PRESENCE OF METHOXIDE IONS : FORMATION OF FULLY UNSATURATED 1,3- AND 1,4-DIAZEPINES
• Studies on Diazepines. XIV. Photolysis of Thieno-, Furo-, and Pyrrolo-[c] pyridine N-Imides : Formation of Novel Fused 1H-1,3- and 3H-2,3-Diazepines
• Studies on Diazepines. VIII. Syntheses and Rearrangements of 3H-1,2-Pyrido- and 3H-1,2-Thieno-diazepines
• Studies on Diazepines. VII. Syntheses of Novel 1H-1,2-Diazepines condensed with Aromatic Heterocyclic Rings
• Syntheses and Thermal Rearrangements of N-Imino-1,2,5,6-tetrahydropyridinium and N-Imino-Δ^3-pyrrolinium Ylides
• エールリッヒ腹水癌に対する2,6-Bis(halomethyl)piperidinesの抗腫瘍性について
• Studies on Seven-Membered Heterocycles. XXXIV. Syntheses and Reactions of 1-Benzosilepines, 1-Benzogermepines, 1-Benzophosphepines, and 1-Benzarsepines
• Synthesis of 1-Benzometalloles Containing Group 14,15,and 16 Heavier Elements via a Common Dilithiostyrene Intermediate
• 薬学教育モデルカリキュラム作成に当っての考え方 : 薬学教育、薬剤師教育に関する基本姿勢
• Studies on Pyridazines. X. Reactivity of 3-Hydroxypyridazine 1-Oxides. (2). Halogenation and Nitration of 3-Hydroxypyridazine 1-Oxides
• Studies on Seven-Membered Heterocycles.XXXI. : Synthesis of 1,4-Oxazepinones and 1,4-Diazepinones from 2-Pyridones and Their Conversion into Fully Unsaturated 1,4-Oxazepines and 1,4-Diazepines
• Studies on Diazepine. XXX. : Addition Reactions of Monocyclic Diazepines with Dimethyl Acetylenedicarboxylate Involving Diazonine Intermediates
• Studies on Diazepines. VI. Photolysis of 1H-1,2-Diazepine and Azepine Epidioxides
• Studies on Pyridazines. XXV. The Ring-opening Reactions of N-Methoxypyridazinium Salts with Nucleophiles
• Studies on Pyridazines. XXIII. Synthesis of N-Substituted 1,4-Dihydropyridazines
• Photo-oxygenation of 1H-1,2-Diazepine and Azepine Derivatives : Formation and Some Reactions of Their Epidioxides
• Studies on Pyridazines. XXIV. The Reaction of Pyridazine N-Oxides and Pyridazinium Ylides with Benzyne
• Photochemistry. XII. Photochemical Behavior of 2-Methyl-3 (2H)-pyridazinone 1-Oxides
• Photochemistry. XI. Photochemical Ring Contraction of 3 (2H)-Pyridazinones to 1-Amino-Δ^3-pyrrolin-2-ones
• Photochemistry. X. Photolysis of Tetrazolo [1,5-b] pyridazines
• A Photochemical Preparation of N-Substituted Pyrroles from Pyridazine N-Oxides
• Photochemistry. VII. Photolyses of Polyphenylpyridazine N-Oxides
• Photochemistry. VI. Photo-induced Methylation of Pyridazines
• The Reaction of Cinnoline 2-Oxides with Phenylmagnesium Bromide
• Studies on Pyridazines. XVIII. Cyanation of 3,3'-Bipyridazines and Their N-Oxides via Their Quaternary Salts
• Studies on Pyridazines. XV. N-Oxidation of 3,3'-Bipyridazines and Reactions of Their N-Oxides
• Studies on Pyridazines. XIV. Syntheses of 3,3'-Bipyridazines
• Studies on Seven-Membered Heterocycles. XXXV. Synthesis of the Group 16 1-Benzoheteroepines Involving the First Examples of 1-Benzotellurepine and 1-Benzoselenepine Rings
• 高ひずみ化合物の原子価異性化を利用した新しい中員複素環化合物の合成
• Studies of Seven-Membered Heterocycles. XXXII. : Synthesis of N-Unsubstituted 1H-1,4-Benzodiazepines Stabilized by Intramolecular Hydrogen Bonding
• Thermal Rearrangements of Cyclic Amine Ylides. VIII. : Intramolecular Cyclization of 2-Ethynylpyridine N-Ylides into Indolizines and Cycl[3.2.2]azines
• Photochemical and Thermal Ring Transformations of 8-Oxa-3,4-diaza- and 3,4,8-Triazatricyclo[5.1.0.0^]oct-4-enes
• THE FIRST EXAMPLES OF ISOLATED N-UNSUBSTITUTED 1H-1,4-BENZODIAZEPINES(Communications to the Editor)
• Studies on Diazepines. XXIX. Syntheses of 3H- and 5H-1,4-Benzodiazepines from 3-Azidoquinolines(Organic,Chemical)
• Studies on Diazepines. XXIV. : Reactions of Monocyclic 1H-1,3-Diazepines. (2). : Photo-Sensitized Oxygenation
• Studies on Diazepines. XXIII. : Reactions of Monocyclic 1H-1,3-Diazepines. (1). : Cycloaddition Reaction with 2,5-Dimethyl-3,4-diphenylcyclopentadienone
• Sigmatropic Rearrangement of Cyclic α-Vinyl Sulfonium Imides : Formation of Thiazocine, Thiazonine, and Thiazecine Derivatives
• Ring Expansion of Cyclic α-Ethynyl Sulfonium Ylides by [2,3]-Sigmatropic Rearrangement : Formation of Thiocin, Thionin, and Thiecin Derivatives
• THERMAL INTRAMOLECULAR CYCLIZATION OF 2-ETHYNYLPYRIDINE N-YLIDES TO INDOLIZINES AND CYCLAZINES
• Thermal Rearrangements of Cyclic Amine Ylides. V. Thermolysis of 6-Ethynyl-1-methyl-1,2,5,6-tetrahydropyridine N-Imides and N-Ylides
• Thermal Rearrangements of Cyclic Amine Ylides. IV. Rearrangement of β, γ-Unsaturated 1-Alkylpiperidine N-Oxides : Formation of 1,2-Oxazepine Derivatives
• Thermal Rearrangements of Cyclic Amine Ylides. III. Intramolecular Cyclization of 2-Ethynylpyridine N-Imides to 3-Azaindolizine Derivatives
• Thermal Rearrangements of Cyclic Amine Ylides. II. Ring-expansion of 4- and 6-Vinyl-1,2,5,6-tetrahydropyridine and 2-Vinylpiperidine N-Imides
• テルロール類および関連化合物の分子内三重結合への環化付加による複素環合成
• Studies on Diazepines. XXII. Synthesis of Monocyclic 1,4-Dihetero Seven-Membered Ring Compounds Using Thermal Valence Bond Isomerization of Tricyclo [4.1.0.0^] heptane Systems
• Photolysis of Pyridazin-3-one 1-Imides : Ring Contraction into 3-Pyrrolin-2-one Derivatives
• Studies on Diazepines. XX. Acylations of 1H-1,2-Thienodiazepines and 1H-1,2-Benzodiazepines
• Studies on Diazepines. XIX. Photochemical Synthesis of 2,3-Benzodiazepines from Isoquinoline N-Imides
• Studies on Diazepines. XVIII. Photochemical Synthesis of 3H-1,3-Benzodiazepines from Quinoline N-Acylimides
• Studies on Diazepines. XVII. Synthesis of Monocyclic 1,3-Diazepines. (2). Substituent Effects on the Thermal Ring-conversion of 1,2-Diazepines into 1,3-Diazepines
• Studies on Diazepines. XVI. Synthesis of Monocyclic 1,3-Diazepines. (1). Thermolysis of 1,2-Diazepines formed from Methylpyridine N-Imides
• Studies on Diazepines. XIII. Photochemical Behavior of Pyrazine, Pyrimidine, and Pyridazine N-Imides
• Studies on Diazepines. XI. Oxidation of 1H-1,2-Benzodiazepines with Lead Tetraacetate : Formation and Some Reactions of Novel 5H-1,2-Benzodiazepines
• Studies on Diazepines. IX. Difference between Photochemical and Thermal Rearrangements of 3H-1,2-Benzodiazepines into 3-Vinylindazoles
• Studies on Diazepines. X. The Sensitized Photooxygenation of 1H-1,2-Benzodiazepines
• Studies on Diazepines. XV. Photolysis of Thieno-, Furo-, and Pyrrolo-[b] pyridine N-Imides : Formation of Fused 1H-1,2- and 3H-1,3-Diazepines
• Studies on Diazepines. XII. Photochemical Synthesis of Novel 1H-1,3-Benzodiazepines from Isoquinoline N-Imides
• Studies on Pyridazines. XI. Reactivity of 3-Hydroxypyridazine 1-Oxides. (3). Nuclear Magnetic Resonance Studies of 3-Hydroxypyridazine 1-Oxide and Its Derivatives
• 3,3'-Bipyridazine Derivatives as Spectrophotometric Reagents for Iron. II
• Photochemistry. IV. Photolyses of 3-Chloro-and 3-Hydroxy-6-phenylpyridazines in Methanol Containing Hydrogen Chloride
• Photochemistry. V. Photocyclization of 3,4,6-Tri- and 3,4,5,6- Tetraphenylpyridazines. Formation of 1,2-Diazapolyarenes
• Photochemistry. II. Formation of Methyl Paraconates and Dimethyl Succinates from Pyridazines
• Photo-induced Oxygenation of Hydrocarbons by Pyridazine N-oxides
• Studies on Pyridazines. XXI. Reaction of 1-Methylpyridazinium Salts with Potassium Cyanide
• Studies on Pyridazines.XX. Syntheses of 1,2-Bis(3'-pyridazinyl)-ethenes, -ethanes, and Their Di-N-oxides
• 1-ベンゾテルロピリリウム塩の化学 : 合成, 構造および反応
• テルル原子の特性を活かした二置換アセチレン類の合成(A・有機化学)
• 台湾におけるシロタテハの生態および食樹について
• Relative Configuration of Sciadin, Dimethylsciadinonate. and Sciadinone, and Substitution of Oxygen in the Lactone Ring of Sciadin with Nitrogen
• Isolation and Structure of New Diterpenes, Dimethylsciadinonate and Sciadinone, from Sciadopitys verticillata
• Studies on Diazepines. V. Syntheses of 3-Substituted 1H-1,2-Benzodiazepines
• Studies on Diazepines. IV. 3H-1,2-Benzodiazepines
• N-アシルアミン類および関連化合物の四酸化ルテニウム酸化
• N-アシルアミン類および関連化合物の四酸化ルテニウム酸化
• 環状アミンN-イミド類の環変換反応
• 1,3-ジアゼピン誘導体の化学
• 1, 2-ベンゾジアゼピンおよび関連化合物の化学
• 総会を縮少して残し, シンポジウムを分科会的に(薬学会の総会・分科会制度の是非)

もっと見る 閉じる

スポンサーリンク