The Pictet-Spengler Reaction of N_b-Hydroxytryptamines and Cysteinals. II. Temperature Effects, Stereochemistry and Mechanism

スポンサーリンク

概要

• 論文の詳細を見る

• The effect of temperature on the Pictet-Spengler reaction of N_b-hydroxytryptamines (1) and cysteinals (2) has been examined. The optically active nitrones (3), obtained from 1 and 2,gave the corresponding N_b-hydroxy-β-carbolines (4α and 4β) exclusively at -78℃ in the presence of an excess of trifluoroacetic acid. The mechanism is discussed in relation to the stereochemistry.

• 社団法人日本薬学会の論文
• 1991-07-25

著者

• 中川 昌子

  Faculty of Pharmaceutical Sciences, Chiba University

• 日野 亨

  Faculty of Pharmaceutical Sciences, Chiba University

• 中川 昌子

  千葉大薬

• 緒方 惟治

  The Chemical Analysis Center Chiba University

• 日野 亨

  千葉大 薬

• 劉 進軍

  School of Pharmacy, Shanghai Medical University

• 緒方 惟治

  Chemical Analysis Center

• 劉 進軍

  School Of Pharmacy Shanghai Medical University

• 中川 昌子

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 中川 昌子

  千葉大 薬

関連論文

• Enantioselective Reduction of meso-Cyclic-1,2-dicarboxylic Anhydrides and 1,2-Dicarboximides : Asymmetric Synthesis of Bicyclic Lactones and Hydroxylactams
• 12 マンザミンAおよびその関連化合物の全合成(口頭発表の部)
• 102(P26) 光学活性イルシナールAの合成研究(ポスター発表の部)
• 54(P18) 海洋産脂質過酸化抑制インドールアルカロイドMartefragin Aの合成と活性(ポスター発表の部)
• 学術貢献賞受賞 村上泰興氏の業績
• 薬学会賞受賞 池上四郎氏の業績
• "夢"と"ロジック"と"アート"とを
• 日本薬学会功労賞受賞, 古賀直文氏の業績
• Decarboxylative C-S Bond Formation. Synthesis of 1,4-Dimethyl-3,6-epidithio-2,5-piperazinedione and Related Compounds
• Synthesis of 3,6-Diethoxycarbonyl-3,6-epidithia-1,4-dimethyl-2,5-piperazinedione and Related Compounds. Formation of C-S Bond by the Reaction of Carbanion and Sulfur Monochloride
• Oxidation of Benzoyl Methionine to Benzoyl Methionine Sulfoxide with 3-Hydroperoxyindolenines
• Studies on Thioamides. I. Synthesis of N-(2-Arylethyl)-thioamides and their Infrared Absorption Spectra.
• The Reductive Cyclization of 1-Methyl-3-aminoalkyloxindoles with Lithium aluminum Hydride.
• Synthetic Approaches to Calycanthaceae Alkaloids. III. Reductive Cyclization of 3,3'-Bioxindoles. (1). A Formation of 5,7-Dimethyl-11b, 11c-bis (2-dimethylaminoethyl)-5,5a, 6a, 7,11b, 11c-hexahydrofuro [2,3-b : 5,4-b'] diindole.
• Synthetic Approaches to Calycanthaceae Alkaloids. II. A Synthesis of 1,1'-Dimethyl-3,3'-bis (2-aminoethyl)-3,3'-bioxindole.
• Tryptophan環状互変異性体の化学
• 日本薬学会学術賞受賞高野誠一氏の業績
• 第5回日仏医薬・精密化学シンポジウム
• 亀谷哲治教授(前会頭, 星薬科大学長)に国際複素環化学会賞授与さる
• 教養としての第2外国語を(薬学教育における第2外国語教育)
• やりくり苦心談
• 放射線障害防護薬剤に関する研究(第15報)インドール系化合物の放射線障害防護効力について
• 放射線障害防護薬剤に関する研究(第8報)システアミン関連化合物の放射線障害防護効力について
• 放射線障害防護薬剤に関する研究(第7報) : AETおよびその関連化合物の放射線障害防護効力について
• Radiation-Protective Agents. V. Synthesis and Hydrolysis of 2-(2-Aminoethylthio) indole Derivatives
• Radiation-Protective Agents. IV. Synthesis of Tetrahydro-β-carbolines and 2-Aminothiazoline Derivative from Tryptophanols
• Reactivities of Radiation-protective Aminoalkylisothiuronium Salts. IV. Stability of N-Ethyl Derivatives of 2-Aminoethylisothiuronium Salt
• Reactivities of Radiation-protective Aminoalkylisothiuronium Salts. II. Spectrophotometric Studies on the Reductivities of 2-Mercaptoethylamine, 2-Mercaptoethyl-, and 3-Mercaptopropyl-guanidine.
• Radiation-protective Agents. II. The Transformation of 2-(2-Aminoethyl)thiopseudoureas to 2-Amino-2-thiazolines
• Radiation-protective Agents.I. Studies on N-Alkylated-2-(2-aminoethyl)thiopseudoureas and 1,1-(Dithioethylene)diguanidines
• Reactivities of Radiation-protective Aminoalkylisothiuronium Salts. I. Hydrogen Ion Liberation of 2-Aminoethylisothiuronium and 3-Amino-propylisothiuronium Bromide Hydrobromide
• On the Reaction of N, N'-Dimethylfumaranilide with Aluminium Chloride
• 66 2-ピリジノン及び2-キノロン誘導体のDiels-Alder反応ダイナミシンA基本骨格合成への応用(ポスター発表の部)
• The ^1H- and ^C-Nuclear Magnetic Resonance Spectra of Manzamine C and Related Compounds
• Alkylation of 3,4-Dihydro-β-carboline
• 53 海産抗腫瘍性アルカロイドマンザミン類の合成研究(口頭発表の部)
• スフィンゴ糖脂質の合成
• The Pictet-Spengler Reaction of N_b-Hydroxytryptamines and Cysteinals. II. Temperature Effects, Stereochemistry and Mechanism
• Reactions of the Cyclic Tautomer of 3-Indoleacetamides. : Synthesis of N_b-Methyl-4,5,6-tribromo-3-indoleacetamide
• 2-Hydroxy-1-substituted-1,2,3,4-tetrahydro-β-carbolines. : The Pictet-Spengler Reaction of N-Hydroxytryptamine with Aldehydes
• 抗ウイルス性海洋天然物ユ-ディストミンの合成
• 1-(1-Pyrrolin-2-yl)-β-carbolines. Synthesis of Eudistomins H, I, and P
• 19 抗ビールス性海洋天然物ユーデストミンの合成 : Pictet-Spengler反応の新展開(口頭発表の部)
• Synthetic Approaches to Fumitremorgins. III. : Synthesis of Optically Active Pentacyclic Ring Systems, and Their Oxidation at Ring C
• 生体内類似反応によるトリプトファン代謝産物の合成研究
• 61 フミトレモルジンBおよび関連化合物の合成
• Inverted Prenylation of N_b-Methoxycarbonyltryptamine. Synthesis of 3a-(1,1-Dimethylallyl) pyrrolo [2,3-b] indole and 2-(1,1-Dimethylallyl) tryptamine Derivatives
• Cyclic Tautomers of Tryptophans and Tryptamines. VIII. Cyclic Tautomers of cyclo-L-Prolyl-L-tryptophyl and Related Compounds
• 28 フミトレモルジン合成へのアプローチ
• Formation and Reactions of the Cyclic Tautomers of Tryptophans and Tryptamines. VII. Hydroxylation of Tryptophans and Tryptamines
• Synthesis of the Imidazo [1,2-a] indole-spirolactone Ring System by Oxidative Double Cyclization. A Synthetic Approach to Tryptoquivalines
• Studies on the Constitutents of Picrodendron baccatum Growing in Indonesia. II. : Structures of Two New Sesquiterpene Lactones, Picrodendrins C and D
• Cyclic Tautomers of Tryptophans and Tryptamines. VI. Preparation of N_a-Alkyl-, 5-Chloro-, and 5-Nitrotryptophan Derivatives
• 22 Tryptoquivaline類合成へのアプローチ : Double cyclizationによる2,3,3a,4-tetrahydro-1H-imidazo[1,2-a]indole-4-Spiro-5'-γ-butyrolactoneの合成
• Stable Sulfur Ylides. XII. : Reaction of 3-Alkyl(aryl)thio-silyloxydienes Derived from Stable Sulfur Ylides with Aromatic Aldehydes. : Synthesis and Structure of Thiolanium Ylides
• 5 ギ酸中でのTryptamine誘導体の増感酸素化反応.rac-Folicanthine,rac-Chimonanthineの合成
• Dye-sensitized Photooxygenation of Tyrptophan : 3a-Hydroperoxypyrroloindole as a Labile Precursor of Formylkynurenine
• Re-examination of the Synthesis of 7,8-Dimethoxy-2-methyl-3-(4', 5'-methylenedioxy-2'-vinylphenyl)iso carbostyril
• GARDNERIA ALKALOIDS PART 14. THE STRUCTURE OF GARDFLORAMINE AND 18-DEMETHOXYGARDFLORAMINE(Communications to the Editor)
• THE STRUCTURES OF ADDITIONAL TELEOCIDIN CLASS TUMOR PROMOTERS
• Bromination of 2-Bromo, 2-Ethylthio, and 2-Ethylsulfonylindoles with N-Bromosuccinimide. Isolation and Reactions of 1-Bromoindoles and 3-Bromoindolenines
• Reaction of Skatole with Iodine in the Presence of Thiourea
• 2-Indolinethiones. Tautomerism and Oxidation to the Disulfides
• Preparation of 3-Arylindoles
• Preparation of 3-Substituted 2-Indolinethiones via Diindolyl Disulfides. The Reaction of 3-Substituted Indoles with Sulfur Monochloride
• オクテット
• Studies on the Bischler-Napieralski Reaction with Unsaturated Lactams. Syntheses of 5,6,9,10,11,12-Hexahydro-2,3-dimethoxybenzo [4,5-a]-benzo [f] quinolizinium and Dihydrosempervirine Salts
• Halogenation of 1-Substituted Skatoles. Preparation of 3-Bromomethylindoles
• Infrared Spectra of Some Indole and Pyrrole Compounds
• Reaction of 1-Phenethyl-2 (1H)-pyridones with Phosphoryl Chloride. Formation of 1-Phenethyl-2-chloropyridinium Salts.
• PHOTOCHEMISTRY OF 2-(3,4,5-TRIMETHOXYPHENYL)-4-(3,4-METHYLENEDIOXYPHENYL)-4-OXO-2-BUTENONITRILE (β-CYANOCHALCONE) : ANOMALOUS DIMERIZATION THROUGH ISOMERIZATION IN THE SOLID STATE
• AILANTHOIDINE, A NOVEL BENZO[C]PHENANTHRIDINE ALKALOID WITH A CYANOPYRIDINE PENDANT, FROM A XANTHOXYLUM SPECIES
• Studies on the Alkaloids of Picrasma quassioides BENNET. VIII. : X-Ray Crystal Structure Analysis of Picrasidine-F
• 94(P12) 有機金属反応を利用した簡易ケトン合成とダイネミシンAモデル合成への応用(ポスター発表の部)
• P-31 光学活性イルシナール類合成へのアプローチ(ポスター発表の部)
• 有機化学者のための蛋白質過剰生産
• Reaction of Tryptamine and Aniline with δ-Valerolactone and Its Dehydro Derivatives. A New Synthesis of 1,2,3,4,6,7,12,12b-Octahydroindolo [2,3-α] quinolizine
• Bromination of 3-tert-Butylindoles with N-Bromosuccinimide
• 有機化学者のための蛋白質過剰生産
• INDOLE ALKALOIDS ISOLATED FROM GELSEMIUM ELEGANS(THAILAND) : 19-(Z)-AKUAMMIDINE, 16-EPI-VOACARPINE, 19-HYDROXYDIHYDRO-GELSEVIRINE, AND THE REVISED STRUCTURE OF KOUMIDINE(Communications to the Editor)
• 抗ウイルス性海洋天然物ユーディストミンの合成
• Pyranoindole and Thiopyranoindole. Oxidative Cyclization of 3-Indolepropanol and 3-Indolepropanethiol with N-Bromosuccinimide, N-Chlorosuccinimide, and Singlet Oxygen
• SYNTHESIS OF (±)-FLUSTRAMINE B, A MARINE ALKALOID
• The Fragmentation of Some Oxindoles and 2-Indolinethiones induced by Electron Impact
• Thiation of Oxindoles
• The Acetylation of 3-Acylindoles
• Indole誘導体の光増感酸素化反応--Tryptophanおよび関連化合物を中心として (天然物化学′80A)
• インド-ル環の反応性--3位側鎖の関与する反応を中心として (現代の生命化学--トリプトファンをめぐって)
• インドール誘導体と酸素分子との反応 : 合成化学と生命化学への貢献を心掛けて
• インドール系化合物の光増感酸素化反応について
• 2-インドリンチオンの化学
• Bromination of Skatole. A Simple Preparation of 3-Methyloxindole and 2-Bromo-3-methylindole.

もっと見る 閉じる

スポンサーリンク