Indoles. II. Oxidation of N-Phthaloyl-1-acetyltryptophan with Chromium Trioxide

スポンサーリンク

概要

• 論文の詳細を見る

• Oxidation of N-phthaloyl-1-acetyltryptophan (1) with chromium trioxide afforded the kynurenine derivative (4) in 35% yield and the dioxindole lactone (6) in 20% yield. The latter substance was separated into the two epimers (6a and 6b) and their configura tion was examined. N-Bromosuccinimide (NBS) in tert-butanol converted N-phthaloyltryptophan (7) to the corresponding oxindole (9) in 51% yield when a 1 : 1 mole ratio of NBS to indole was used. When a 2 : 1 ratio of reactants was used and its products were treated with sodium hydrogen carbonate, the dioxindole lactone (8) was obtained, and acetylation of 8 afforded 6 that agreed with the oxidation product. The mass spectra of 8 and 9 are discussed.

• 公益社団法人日本薬学会の論文
• 1971-03-25

著者

• 大木 貞雄

  Tokyo College of Pharmacy

• 長坂 達夫

  Tokyo College of Pharmacy

• 大木 貞雄

  東京薬科大学

• 長坂 達夫

  Tokyo University Of Pharmacy And Life Science School Of Pharmacy

関連論文

• Studies on Optically Active Amino Acids. V. Synthesis of Optically Active α-Aminoalcohols by the Reduction of α-Amino Acid Esters with Sodium Borohydride
• Synthesis of Pyrrolidine Derivatives with Pharmacological Activity. XII. : Synthesis and Anticholinergic Activity of 1,1-Dialkyl-3-diphenylmethylene-2,4-dimethylpyrrolidinium Halides
• Synthesis of Pyrrolidine Derivatives with Pharmacological Activity. XI. The Lora-Tamayo Reaction of 3-Methyl-1,1-diphenyl-1,4-butanediol with Acetonitrile-Stannic Chloride Complex. Synthesis of 1,2,5-Trimethyl-3-diphenylmethylenepyrrolidines
• ピロリジン系薬理作用物質の合成研究(第9報)抗アセチルコリン作用物質, 1,1,5-Trimethyl-2-ethyl-および1,1,2,4,5-Pentamethyl-3-diphenylmethylenepyrrolidinium Iodideの合成
• 5-Aminophthalazine誘導体の合成
• Cyclic Imidesの還元(第2報)α-置換-Succinimideおよび-GlutarimideのSodium Borohydride還元, およびその反応機構について
• Cyclic Imidesの還元(第1報)α-Methyl-およびα, α-DimethylsuccinmideのSodium Borohydride還元および還元成績体より3-Diphenylmethylene-1,1,2,4,4-pentamethylpyrrolidinium Iodideの合成
• Indoles. III. A New Synthesis of 4-Indolecarboxylic Acid
• ピロリジン系薬理作用物質の合成研究(第5報) : α-Cycloalkyl-α-phenyl-3-pyrrolidinemethanol類の合成
• Synthesis of Pyrrolidine Derivatives with Anticholinergic Properties. IV. Synthesis, Stereochemistry, and Pharmacological Activity of N, N-Diethyl- and N, N-(epimeric)-Ethylmethyl-2-methyl-3-diphenylmethylenepyrrolidinium Salts
• 抗アセチルコリン作用を有するピロリジン誘導体の合成 (その2) : 1-Alkyl-2-methyl-2-pyrrolineのエナミン反応について
• 抗アセチルコリン作用を有するピロリジン誘導体の合成 (その1) : 1-Alkyl-3-(diphenylhydroxymethyl)pyrrolidine類の合成
• Cyclization towards Carbon-Carbon Double Bond. III. A New Synthesis of 1-Pyrroline Derivatives and a Synthesis of 1,2-Dialkyl-3-diphenyl-methlenepyrrolidine Alkyl Halide, an Anti-acetylcholine Substance
• Synthesis of Quinolizine Derivatives. XIII. On the Relationship between Chemical Structure and Uterus Contracting Action of Quinolizidine Derivatives, and Synthesis of Some of these Derivatives.
• Synthesis of Chiral Pyrrolidine Derivatives from (S)-Pyroglutamic Acid. I : 7-Substituted (2R, 5S)-2-Aryl-1-aza-3-oxabicyclo[3.3.0]octan-8-ones, 7-Substituted (2R, 5S)-2-Aryl-1-aza-3-oxabicyclo[3.3.0]oct-6-en-8-ones and 3-Substituted (S)-5-(Hydroxymethyl)
• ビロリジン系薬理作用物質の合成研究(第10報)抗アセチルコリン作用物質1,1-Diethyl-および1,1-(epimeric)-Ethylmethyl-2-methyl-4-diphenylmethylenepyrrolidinium Iodidesの合成
• Anticholinergic Agents. Synthesis of 4-Diphenylmethylene-1,1,2,3-tetramethylpyrrolidinium Iodide
• Anticholinergic Agents. Synthesis of 1,1,4-Trimethyl- and 1,1,5-Trimethyl-3-diphenylmethylenepyrrolidinium Halides
• Diphenylmethylene-γ-butyrolactone類の合成およびアミンとの反応について
• Aza-steroids.III.Synthesis of 17-Acetoxy-10-aza-androstan-7-one and Related Compounds
• Aza-steroids. II. Enamine Reaction of Androstanones. Synthesis of 17-Acetoxy-5β-androstano [4,3-c] quinolizidin-2'-one
• キノリチン誘導体の合成研究(第23報) : Perhydrobenzo[c]quinolizineおよびBenzo[c]quinolizine誘導体の合成
• Hofmann Degradation of Quinolizidine (Synthesis of Quinolizine Derivatives. XXII)
• Aza-steroids. I. Synthesis of 9-Aza-steroid Ring System
• Synthesis of Quinolizine Derivatives. XX. Synthesis and Stereochemistry of Perhydrobenzo [c] quinolizine
• Reduction of Cyclic Imides. III. Reduction of 3- and 4-Substituted Phthalimides with Sodium Borohydride
• 東薬大一医療薬学大学院のめざすもの
• Photo-induced 1,3-Dipolar Cycloaddition Reaction of Aziridinedicarboximide
• Attempted Synthesis of 4,5-Epiminotetrahydro-1,2-oxazine
• 5-(1-ピロリジニル)-, 5-(1-ピペリジニル)-及び5-(4-モルフォリニル)-3-ジフェニルメチレン-2-ピロリジノンの合成
• Synthesis of 5-endo-Benzoyloxy-N-[amino (lower) alkyl] bicyclo [2. 2. 1] heptane-2,3-di-endo-carboxylic Acid Imides as Potential Antiarrhythmia Agents
• Synthesis of Quinolizine Derivatives. XVIII. Diastereoisomers of 3-(4-Chlorobenzyl) quinolizidine, and Uterus-contracting Agent, and 3-Lupinine
• Synthesis of Quinolizine Derivatives. XVI. Synthesis of 3-(Subst.-benzyl)quinolizidine
• Synthesis of Quinolizine Derivatives. IX. Synthesis of 3,3'-Polymethylenediquinolizidine
• スパルティンより誘導される含窒素複素環化合物(第3報) : スパルティンのHofmann分解(キノリチン誘導体の合成 第19報)
• スパルテインより誘導される含窒素複素環化合物(第2報) : 5-Hydroxysparteine(Retamineの立体異性体)および5-Hydroxymethylsparteineの合成 : キノリチン誘導体の合成 第15報
• Nitrogen-containing Heterocyclic Compounds derived from Sparteine. I. Synthesis of 5-Oxosparteine
• Hydroxymethyl-β-carboline誘導体の合成
• 1,3-二置換1,2,3,4-テトラハイドロ-β-カルボリン誘導体の合成およびその立体異性体の研究
• Indoles. V. Syntheses and Reactions of Cycloalkanon-[c, d] indole Derivatives
• インドール類(第4報)1-アセチルトリブトファン誘導体の混酸によるニトロ化反応
• Indoles. II. Oxidation of N-Phthaloyl-1-acetyltryptophan with Chromium Trioxide
• Studies on Benzimidazoles and Related Compounds. V. Reaction of 2-Azido-1-methylbenzimidazole with Unsaturated Compounds
• Synthesis of 1H-Pyrrolo [1,2-α] indole Derivatives. II. Synthesis of 7-Nitro-2,3,9,9a-tetrahydro-1H-pyrrolo [1,2-α] indoles
• Synthesis of 1H-Pyrrolo [1,2-α] indole Derivatives. I. Synthesis of 6H-Isoindolo [2,1-α] indoles by the Harley-Mason Method
• Studies on Benzimidazoles and Related Compounds. IV. Reactivity of 2-Azido-1-methylbenzimidazole
• Synthesis of Nitrogen-containing Heterocyclic Compounds through Nitrilium Salt. II. Reaction of Nitriles with 2-(2-Hydroxycyclohexyl) ethanol and 1-(2-Hydroxycyclohexyl) propan-2-ol in the Presence of Acid
• Synthesis of Nitrogen-containing Heterocyclic Compounds through Nitrilium Salt. I. Reaction of Nitriles with 2-(α-Hydroxymethyl, -ethyl, and -isopropyl) cyclohexanol in the Presence of Acid
• 抗アセチルコリン作用物質の合成 : Aminoethyl 4,4-Diphenyl-3-butenoate, 4,4-Diphenyl-3-butenamideおよび4,4-Diphenyl-4-hydroxybutyramide類の合成
• Synthesis of Pyrrolidine Derivatives with Anticholinergic Properties. III. Syntheses and Stereochemistry of 1,2,5-Trimethylpyrrolidine and 3-(Diphenylmethylene)-1,2,5-trimethylpyrrolidine
• ピロリジン系薬理作用物質の合成研究(第6報) : 1,2-Dimethyl-3-[bis(2-thienyl)-methylene]pyrrolidineおよび1-[1,1-Bis(2-thienyl)-3-propenyl]-2-methylpyrrolidineの合成
• SYNTHESIS OF LENNOXAMINE via THE INTRAMOLECULAR CYCLIZATION OF ALKYNYLAMIDE
• 五員環アミンの合成と反応Prifinium Bromideの合成を中心として
• Indoles. I. Syntheses of 1-Acetyltryptophan and Its Derivatives, and Their Friedel-Crafts Reaction

もっと見る 閉じる

スポンサーリンク