Ring Expansion Reaction of 2,2-Dimethyl-2,3-dihydrobenzo [b]-thiophene N-(p-Toluenesulfonyl) sulfilimine

スポンサーリンク

概要

• 論文の詳細を見る

• The ring expansion reactions of 2,2-dimethyl-2,3-dihydrobenzo [b] thiophene N-(p-toluenesulfonyl) sulfilimine (5) were investigated. Refluxing 5 in benzene gave the dihydrobenzo [b] thiophene 7 (60%) and the unsymmetrical dimer 13 (18%) as major products. Refluxing 5 in acetic acid gave a mixture of the dihydrobenzo [b] thiophene 8 and the thiochroman 11 in 76% total yield (ratio 2.6 : 1), while refluxing 5 in methanol afforded the dihydrobenzo [b] thiophene 9 and the thiochroman 12 in 58% total yield (ratio 1 : 5). The reaction of 5 with 2-mercaptobenzothiazole in refluxing toluene afforded exclusively the dihydrobenzo [b] thiophene 10. These results were rationalized in terms of the intermediacy of the sulfenamide 15 and thiiranium ion 16.

• 社団法人日本薬学会の論文
• 1980-05-25

著者

• 田村 恭光

  Faculty Of Pharmaceutical Sciences Osaka University

• BAYOMI SAIDMOHAMAD

  Faculty of Pharmaceutical Sciences, Osaka University

• 池田 正澄

  Faculty of Pharmaceutical Sciences, Osaka University

• 池田 正澄

  Kyoto Pharmaceutical University

• Bayomi Saidmohamad

  Faculty Of Pharmaceutical Sciences Osaka University

• 黄瀬 正博

  Research Laboratories, Nippon Shinyaku Co., Ltd.

• 黄瀬 正博

  Nippon Shinyaku Company, Ltd.,

• 黄瀬 正博

  Nippon Shinyaku Company Ltd.

• 黄瀬 正博

  Research Center Sumitomo Pharmaceuticals Co. Ltd

関連論文

• Synthesis of 2-(Heteroarylthiomethyl)-1β-methylcarbapenem via Propargylation of 4-Acetoxy-2-azetidinone with 3-Methyl-1-tributylstannylallene
• Hypervalent Iodine Oxidation of Ethynylcarbinols : A Short and Efficient Conversion of Dihydroxyacetonyl Groups from Keto Groups
• Hypervalent Iodine Oxidation of α,β-Unsaturated Carbonyl Compounds(Organic,Chemical)
• Pummerer-Type Reaction of α-Acylsulfides Using Phenyl Iodosyl Bis(trifluoroacetate)
• Oxidative 1,2-Aryl Migration of Alkyl Aryl Ketones by Using Diacetoxyphenyliodine : Syntheses of Arylacetate, 2-Arylpropanoate, and 2-Arylsuccinate
• Synthesis of 2-Arylsuccinates by Oxidative 1,2-Aryl Migration of 3-Aroylpropionic Acids or 5-Arylfuran-2 (3H)-ones with Thallium (III) Nitrate
• Synthesis of Diclofenac
• The Reaction of Vinyl Sulfones with Iodine Azide : Synthesis and Thermal Reactions of β-Azidovinyl Sulfones
• Syntheses of Arenediacetic Esters and Acetonyl-Substituted Arylacetic Esters by Means of Friedel-Crafts Reaction with α-Acyl-α-chlorosulfides
• Syntheses of Arylacetone and Arylacetonitrile by Friedel-Crafts Reaction with α-Chloro-α-(methylthio)-substituted Acetone and Acetonitrile
• 4 Securinine及びVirosecurinineの全合成
• Total Synthesis of Securinine
• Asymmetric Synthesis Using Chiral Acetals : Highly Stereoselective Reduction of Chiral α-Keto-β, γ-unsaturated Acetals and Its Application for the Synthesis of (R)-(-)- and (S)-(+)-3'-Methoxy-4'-O-methyljoubertiamine
• Asymmetric Synthesis Using Chiral Acetals : Highly Diastereoselective Nucleophilic Addition of Grignard Reagents to Chiral 1-Oxo-β-tetralone 1-Acetals
• Asymmetric Synthesis Using Chiral Acetals : Highly Diastereoselective Addition of Organocerium Reagents to Chiral α-Aldoxime-Ether Acetal
• Asymmetric Synthesis Using Chiral Acetals : Studies on the Nucleophilic Addition of Organometallics to Chiral α-Keto Acetals in Open-Chain Systems(Organic,Chemical)
• Asymmetric Synthesis Using Chiral Acetals : Studies on the Nucleophilic Addition of Organometaltics to Chiral α-Keto Acetals in Cyclic Systems(Organic,Chemical)
• Synthetic Anthracyclines : Total Synthesis of D-Ring Pyridine and Pyrazine Analogues of 11-Deoxydaunomycin
• Synthetic Anthracyclines : Regiospecific Total Synthesis so D-Ring Thiophene Analogues of Daunomycin
• Total Synthesis of 11-Deoxyanthracyclines : 4-Demethoxy-11-deoxy-daunomycin : 11-Deoxydaunomycin, and Their Analogues
• An Efficient, Regiospecific Synthesis of 4-Demethoxydaunomycinone and Daunomycinone(Organic,Chemical)
• Synthesis of the Erythrinan Skeleton by Acid-Promoted Cyclization of N-(3-Oxo-1-cyclohexen-1-yl)-N-[2-(3,4-dimethoxyphenyl) ethyl]-α-(methylsulfinyl) acetamide
• Reaction of Benzo [b] furan and 1-Acylindoles with Iodine Azide
• Synthesis and Some Chemical Transformations of 2-Azidomethylindoles
• Synthesis and Thermolysis of 3-Azidoindolenines
• Ring Expansion Reaction of 2,2-Dimethyl-2,3-dihydrobenzo [b]-thiophene N-(p-Toluenesulfonyl) sulfilimine
• The Base-induced β-Elimination Reaction of 1,1,1-Trisubstituted Hydrazinium Salts
• N-Acylimino-3,4-dihydroisoquinolinium Betaineの合成とその性質について
• 2,7-Dioxo-1,2,3,4,4_a, 5,6,7-octahydroquinolineのN-Bromosuccinimideによる芳香化反応
• Structure of Securitinine.
• Convenient Synthesis of 6-(1-Acetyl-2-piperidyl)-6-hydroxy-2-cyclohexene-Δ^-acetic Acid γ-Lactone, the Key Intermediate in Total Synthesis of Securinine
• Structure of Securitinine
• Hofmann Degradations of Tetrahydrosecurinine and Tetrahydrosecurininol. Stereochemistry at C-3a of Tetrahydrosecurinine
• Synthesis and Stereochemistry in B/C Ring Juncture of Lactamcarbinol A, a Degradation Product of Securinine
• Gas Chromatography of Aromatic Acids
• A Novel Oxidative Intramolecular [4+2]Cycloaddition of Silylene-Protected Dihydroxystyrene Derivatives Leading to peri-Hydroxy Polycyclic Aromatic Compounds : A Synthesis of the ABCD Ring System of Frederucamycin A
• Strong Base-Induced Cycloaddition Reaction of Homophthalic Anhydride with Aldehydes
• 15.Securitinine及びSecurinol Aの構造
• Structures of Norsecurinine and Dihydronorsecurinine
• Absolute Stereochemistry at C_ of Norsecurinine and Dihydronorsecurinine
• Structure and Stereochemistry of Norsecurinine and Dihydronorsecurinine
• Stereochemistry of Alkylation of Cyclic β-Ketosulfoxides. III. Alkylation and Deuteration of the Dianion of Isothiochroman-4-one 2-Oxide
• Stereochemistry of Alkylation of Cyclic β-Ketosulfoxides. II. Alkylations of 2-Methylbenzo [b] thiophen-3 (2H)-one 1-Oxide
• Stereochemistry of Alkylation of Cyclic β-Ketosulfoxides. I. Alkylations of 3-Methylisothiochroman-4-one 2-Oxide and 2-Methylthian-3-one 1-Oxide
• Reaction of the α, α'-Dianion of β-Ketosulfoxide
• Synthesis of Ethyl Arylacetates by Means of Friedel-Crafts Reaction of Aromatic Compounds with Ethyl α-Chloro-α-(methylthio) acetate
• Synthetic Anthracyclines : Regiospecific Total Synthesis of a D-Ring Indole Analogue of Daunomycin
• Synthesis of 5-(2-Allylamino-1-hydroxyalkyl)-8-hydroxycarbostyrils, New β-Adrenoceptor Stimulants
• Synthesis of 8-Hydroxycarbostyril
• Photochemical and Thermal Behavior of 2-Benzoyl-3-ethoxycarbonyl-methylcyclohex-2-enone and Its Derivatives
• Reaction of 2-Aroylcyclohex-2-enones with Hydroxylamine. Isoxazole Ring Formation
• Studies on Ergot Alkaloids and Related Compounds. XIII. syntheses and Stereochemistries of 4-Methyl-1,2,3,-4,4a, 5,6,10b-octahydrobenzo[f]quinoline-2-carboxylic Acids
• Olefin Cyclization Initiated by α-Thiocarbocation : A Novel Route to Pyrrolizidine Alkaloids
• Chemistly of O-Silylated Ketene Acetals : Stereocontrolled Synthesis of 3-Benzoylamino-2,3-dideoxy-pentoses by a 1,3-Addition to Chiral Nitrones
• The Chemistry of O-Silylated Ketene Acetals : Synthesis of N-Benzoyl-L-daunosamine
• Chemistry of O-Silylated Ketene Acetals. Novel Chemical Transformation of Vinyl Sulfoxides and Related Sulfoxides(Organic,Chemical)
• アントラサイクリン系抗生物質の合成研究--ホモフタル酸無水物および関連化合物の環化付加反応
• Rearrangement in Dihydroresorcinol Derivatives. XI. Photolysis and Thermolysis of 3-Azido-2-cyclohexen-1-ones and 2-Cyclopenten-1-ones
• Syntheses and Pharmacological Properties of 2- and 3-Aralkyltetrahydro-1,3-oxazines
• Adsorption Equilibria of Trimethylamine on Porous Adsorbents
• 26 Anthracyclinoneの合成
• Studies on Azasteroids and Related Compounds.I. The Reaction of Ethyl 2-Piperidineacetate with 2-Tetralone
• Isolation of Securinol A, B, and C from Securinega suffruticosa REHD. and the Structures of Securinol A and B
• Synthetic Studies on η-Pyrromycinone. V. Total Synthesis of η-Pyrromycinone
• Synthetic Studies on η-Pyrromycinone. IV. Conversion of 1,11-Dimethoxy-5(12H)-naphthacenones into 4,6-Dimethoxynaphthacenequinones by Chromium Trioxide Oxidation
• Synthetic Studies on η-Pyrromycinone. III. Intramolecular Cyclization of methyl 2-Ethyl-5-hydroxy-6-(2-carboxy-3,6-dimethoxybenzoyl)-1-naphthoate
• Synthetic Studies on η-Pyrromycinone II. Synthesis of Methyl 2-Ethyl-5-Hydroxy-1-naphthoate
• Reactions of 1-Methyl-1H-1,2,4-triazolium 4-Imine and 4-Acylimines with Acetylenic Esters
• Chemistry of O-Silylated Ketene Acetals : Preparation of α-Siloxy Phenyl Sulfides and Methyl 3-(Phenylthio) butyrates from Alkyl Phenyl Sulfoxides
• Synthesis and Some Properties of 2-Azathiabenzene 1-Oxides
• Nucleophilic Reactions of N-Unsubstituted Sulfoximines with Activated Acetylenes, Olefins, and Diphenylcyclopropenone
• Degradations of Allosecurinine
• Optical Rotatory Dispersion and Circular Dichroism of Securinine and Allosecurinine
• 1,3-Dipolar Cycloaddition Reaction of 1-Methylperimidine 3-Ylides with Dimethyl Acetylenedicarboxylate
• Cationic Polar Cycloadditions of Phenylthionium Ions with Olefins : A New Route to Thiochromans
• Intramolecular [2+2] Photocycloaddition of 2-[N-Acyl-N-(2-propenyl)-amino] cyclohex-2-enones : Synthesis of 2-Azabicyclo [2.1.1] hexanes
• INTRAMOLECULAR PHOTO [2+2] CYCLOADDITION OF 2-ALLYLOXY-AND 2-ALLYLAMINOCYCLOHEX-2-ENONES : FORMATION OF 2-OXA-AND 2-AZA-BICYCLO [2.1.1] HEXANE SYSTEMS
• Synthesis of 8-Methoxy-and 8-Methoxy-6-methylhomophthalic Anhydrides, Key Intermediates for the Synthesis of Anthracyclinones and peri-Hydroxylated Polycyclic Aromatic Compounds
• Linearly Condensed peri-Hydroxy Aromatic Compounds Derived from the Cycloaddition Reaction of Homophthalic Anhydrides with Dienophiles
• Rections of 2-Benzoyl-3-chloro-2-cyclohexen-1-ones with Some Organometallic Compounds
• Photochemical Dealkylation of 2-Acyl-3-alkylamino-5,5-dimethyl-2-cyclohexen-1-ones
• Synthesis and Photocyclization of 2-Aroyl-3-methylcyclohex-2-enones
• Studies on Ergot Alkaloids and Its Related Compounds. X. Condensation of Cyclic Ketones and 3-Methylaminopropionates
• 複素環化合物の開環反応の研究(第6報) : N-(3-Oxo-1-cyclohexenyl)-pyridinium Chlorideと求核試薬との反応
• O-Arenesulfonyl-N-alkylhydroxylamines as Aminating Reagents
• Photolysis and Thermolysis of 3-Diazothiochroman-4-one and Related Compounds
• Synthesis, Stereochemistry, and Rearrangement of N-Tosylsulfilimines and (Bismethoxycarbonyl) methylides of 1,4-Dimethylthioxanthene and Its 9-Alkyl Derivatives
• 1,2-Diaminopyridinium塩とα, β-不飽和カルボニル化合物との反応
• Synthesis of 1-Carbethoxyindolizines via Intramolecular 1,5-Cyclization of Ylides
• Formation of Indolizines via Pyridinium 3-Carbomethoxyallylides
• Preparation of 5-Aminothiazole-4-carboxylic Acid Derivatives
• Monomethylation of Aromatic Rings by Friedel-Crafts Reaction with Chloromethyl Sulfide
• The Photorearrangement and Thermolysis of N-Benzoyliminoisoquinolinium and Quinolinium Betaines
• Intramolecular Photo [2+2] cycloaddition of 2-Alkenoyloxycyclohex-2-enones
• 5-Hydroxy-and Methoxy-1-(tert-aminoalkyl)-3,4-dihydrocarbostyrilの合成
• Stereospecific Epoxidation of cis-2-Butene-1,4-diones to cis-2,3-Epoxybutane-1,4-diones with Oxodiperoxomolybdenum (VI), MoO_5・H_2O・HMPA
• Reactions of Thiocarbamoylaminophosphonium Salts obtained from Amines and the Combined Reagent, Triphenylphosphine-Thiocyanogen (TPPT) : Preparation of Thioureas, Acylthioureas and Amides
• Reactions of Cyclic-enaminoketones with Diacylethylenes. Regioselective Synthesis of 4-Oxotetrahydroindole, 5-Oxotetrahydroquinoline, Pyrrolo- and Pyrido [2,3-d] pyrimidines
• N-Alkylation of Ethyl 1,4-Dihydro-4-oxopyridine-3-carboxylates via Their Thallium (I) Salts
• Cycloaddition to 1,3-Dialkoxycarbonylallenes : One-Step Synthesis of Heterocyclic Compounds Containing a Dialkyl Glutaconate Structure

もっと見る 閉じる

スポンサーリンク