Decarboxylative C-S Bond Formation. Synthesis of 1,4-Dimethyl-3,6-epidithio-2,5-piperazinedione and Related Compounds

スポンサーリンク

概要

• 論文の詳細を見る

• Heating of dipotassium salt of 3,6-dicarboxy-1,4-dimethyl-2,5-piperazinedione (4) with sulfur monochloride in dioxane gave 1,4-dimethyl-3,6-epidithio-2,5-piperazinedione (11) in 33% yield with simultaneous decarboxylation. When the reaction mixture from 4 and S_2Cl_2 was reduced with NaBH_4 and ethylated with ethyl iodide, cis 3,6-bis (ethylthio) derivative (17) was obtained in 50% yield besides a trace amount of trans isomer (18) and the monoethylthio derivative (19). Reactions of other metal salts (16a, 16b, and 16c) with S_2Cl_2 did not improve the yield of 11. On the other hand the reaction of 4 with ethanesulfenyl chloride in dioxane did not yield 17,but gave 18,19,and hydroxylated compounds (20,21,and 22) in low yields. Similar results were obtained in the reaction of 4 with benzenesulfenyl chloride. The mechanism of the decarboxylative C-S bond formation was also discussed.

• 社団法人日本薬学会の論文
• 1976-02-25

著者

• 日野 亨

  Faculty of Pharmaceutical Sciences, Chiba University

• 佐藤 忠夫

  Faculty Of Pharmaceutical Sciences Chiba University

• 日野 亨

  The Chemical Analysis Center Chiba University:faculty Of Pharmaceutical Sciences Chiba University

関連論文

• Enantioselective Reduction of meso-Cyclic-1,2-dicarboxylic Anhydrides and 1,2-Dicarboximides : Asymmetric Synthesis of Bicyclic Lactones and Hydroxylactams
• The ^1H- and ^C-Nuclear Magnetic Resonance Spectra of Harman. Reinvestigation of the Assignments by One- and Two-Dimensional Methods
• 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
• Nuclear Magnetic Resonance Studies on Schiff Base and Related Compounds derived from Pyridoxal
• 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.
• On the Reaction of N, N'-Dimethylfumaranilide with Aluminium Chloride
• The ^1H- and ^C-Nuclear Magnetic Resonance Spectra of Manzamine C and Related Compounds
• Alkylation of 3,4-Dihydro-β-carboline
• 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
• 1-(1-Pyrrolin-2-yl)-β-carbolines. Synthesis of Eudistomins H, I, and P
• Synthetic Approaches to Fumitremorgins. III. : Synthesis of Optically Active Pentacyclic Ring Systems, and Their Oxidation at Ring C
• 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
• 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
• Cyclic Tautomers of Tryptophans and Tryptamines. VI. Preparation of N_a-Alkyl-, 5-Chloro-, and 5-Nitrotryptophan Derivatives
• Dye-sensitized Photooxygenation of Tyrptophan : 3a-Hydroperoxypyrroloindole as a Labile Precursor of Formylkynurenine
• 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
• Stereochemical Studies. XXIII. Stereochemistry of the Thermal Isocyanide-Cyanide Rearrangement
• 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
• Stereochemical Studies. XXII. Thermal Rearrangement of S(-)-1-Phenylethyl Isocyanide
• Halogenation of 1-Substituted Skatoles. Preparation of 3-Bromomethylindoles
• Purines. V. The Dimroth Rearrangement of 1-Alkoxyadenines : The Synthesis of N-Alkoxyadenines
• Bromination of 3-tert-Butylindoles with N-Bromosuccinimide
• 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 Acetylation of 3-Acylindoles

もっと見る 閉じる

スポンサーリンク