Studies on the Reactions of Heterocyclic Compounds. VI. 1,3-Dipolar Cycloaddition Reaction of Disubstituted Methylides of Isoquinoline and Pyridine with Acetylenic Compounds
スポンサーリンク
概要
- 論文の詳細を見る
Tetramethyl 3,10b-dihydropyrrolo [2,1-α] isoquinoline-1,2,3,3-tetracarboxylate (VI) was isolated for the first time as the primary addition product of a reaction between isoquinolinlium bis (methoxycarbonyl) methylide (V) and dimethyl acetylenedicarboxylate (IV). Treatment of VI with hydrogen chloride and then with potassium carbonate resulted in its isomerization into 2,3-dihydropyrrolo [2,1-α] isoquinoline derivative (VII). In the reaction of isoquinolinium dicyanomethylide (XI) with IV, the isomerized 2,3-dihydro compound (XIII) and the eliminated product (XIV) were produced, instead of their primary adduct (XII). The relation between a substituent group in the 2,3-dihydrotype compounds and their reactivity was examined. On the other hand, in the reaction of disubstituted pyridinium methylides with acetylenic compounds, only aromatized products were obtained.
- 公益社団法人日本薬学会の論文
- 1972-07-25
著者
-
小林 義郎
Tokyo College of Pharmacy
-
藤山 和男
Faculty Of Pharmaceutical Sciences Osaka University
-
関根 安男
Research Foundation Itsuu Laboratory
-
久津間 輝雄
Tokyo College of Pharmacy
-
久津間 輝雄
Tokyo College Of Pharmacy:(present Address) Research Laboratories Ohta Seiyaku Co. Ltd.
関連論文
- Quantitative Structure-in Vivo Half-Life Relationships of Perfluorochemicals for Use as Oxygen Transporters
- Amino Acids and Peptides. XXIII. Leu-Enkephalin Analogs Containing a Fluorinated Amino Acid at Position 2,4 or 5
- Structure-Activity Relationship of Fluorine-Containing Renin Inhibitory Peptides Based upon the Tertiary Structure of Human Renin
- Synthesis and Biological Activity of Fluorine-Modified Platelet Activating Factors(Medicinal Chemistry,Chemical)
- Studies on Organic Fluorine COmpounds. IL. The Ene Reaction of Trifluoroacetone
- Studies on Organic Fluorine Compounds. XLIII. The Ene Reaction of Hexafluoroacetone
- Studies on Organic Fluorine Compounds. XLI. The Friedel-Crafts Reaction of Trifluoropropene
- Synthesis and Biological Activity of 1α-Fluoro-25-hydroxyvitamin D_3
- Studies on Organic Fluorind Compounds. LII : Synthesis and Biological Activity of 26,26,26,27,27-Pentafluoro-1α-hydroxy-27-methoxyvitamin D_3
- Studies on Organic Fluorine Compounds. II. Mass Spectrometry of Trifluoromethylated Pyridines.
- Syntheses of Ten-membered Ring Amine Derivatives and 1-Azabicyclo-[4,4,1] undecane from 3,4,6,7,8,9-Hexahydro-2H-quinolizine
- Studies on the Reaction of Heterocyclic Compounds. XV. N-Alkylation of 1,2,3,4-Tetrahydro-5-methyl-1,6-naphthyridine
- Studies on the Reactions of Heterocyclic Compounds. XIV. 1,3-dipolar Cycloaddition of Some Isoquinolinium Ylides with Methyl Propiolate
- STEREOSELECTIVE SYNTHESIS OF TRIFLUOROMETHYLATED OLEFIN AND DIENE
- Studies on Organic Fluorine Compounds. XLVII. Synthesis of Trifluoromethylated Sugars through the Aldol Reaction of 2-Trimethylsilyloxy-4-trifluoromethylfuran
- Studies on Organic Fluorine Compounds. VII. Trifluoromethylation of Aromatic Compounds
- Studies on Organic Fluorine Compounds. XLVI. Synthesis of 4-Trifluoromethyl-2 (5H)-furanone and 4-Trifluoromethyl-N-substituted Dihydropyrrol-2-ones
- Studies on Organic Fluorine Compounds. XLV. Synthesis and Regioselective Substitution Reaction of 3-Trifluoromethylfuran
- SYNTHESIS OF TRIFLUOROMETHYLATED LACTONE AND EPOXIDE
- TRIFLUOROMETHYLATION OF CHIRAL ALDEHYDE AND SYNTHESIS OF 6-DEOXY-6,6,6-TRIFLUOROHEXOSES
- Synthesis of Fluorinated Retinal : A C_6-C_7 s-trans Fixed Retinal Containing a Trifluoromethyl Group at the Terminal Position of the Conjugated System
- TRIFLUOROMETHYLATED ALLYLIC ANION AND RADICAL : GENERATION BY THE ELECTRONIC INVERSION OF II-ALLYLICPALLADIUM COMPLEX BY SAMARIUM DIIODIDE
- PALLADIUM(0)-CATALYZED REACTIONS OF TRIFLUOROMETHYLATED ALLYLIC ESTER DERIVATIVES : SYNTHESIS OF TRIFLUOROMETHYLATED CHRYSANTHEMIC ACID ESTER
- ENANTIOSELECTIVE REDUCTION OF FLUOROALKYL ALKYNYL KETONES : ENORMOUS ELECTRONIC EFFECT OF THE TRIFLUOROMETHYL GROUP(Communications to the Editor)
- SYNTHESIS OF 5-FLUOROARACHIDONIC ACID AND ITS BIOTRANSFORMATION TO 5-FLUORO-12-HYDROXYEICOSATETRAENOIC ACID(Communications to the Editor)
- KINETIC RESOLUTION OP FLUORQALKYL (E)-VINYL CARBINOL DERIVATIVES BY ASYMMETRIC EPOXIDAT1QN WITH TITANIUM-TARTRATE CATALYSTS(Communications to the Editor)
- Studies on Organic Fluorine Compounds. L. Synthesis and Biological Activity of 2α-Fluorovitamin D_3
- Trifluoromethylation with Bromotrifluoromethane
- Studies on Organic Fluorine Compounds. XLIV. The Diels-Alder Reaction of Trifluoromethylated Cyclopropenyl Ketone and Its Imine
- Studies on the Organic Fluorine Compounds. XXIV. Photochemical Trifluoromethylation of Aromatic Compounds
- Studies on Organic Fluorine Compounds. XXI. Isomerization of Fluorinated Dewar Pyridine Derivative and Its Metal Complexes
- Studies on Organic Fluorine Compounds. XX. Synthesis and Reactions of a Substituted Dewar Pyridine
- Studies on Organic Fluorine Compounds. XIX. Synthesis and Reactions of"Dewar"Thiophene
- Studies on Organic Fluorine Compounds. XVI. : Stereochemistry in Fluorination of Sterols with Phenylfluorophosphoranes
- Studies on Organic Fluorine Compounds. XIII. Studies on Equilibrium of (Trifluoro- and/or Chlorodifluoromethyl)-dihydro-s-triazine Derivatives by ^F-Nuclear Magnetic Resonance Spectra
- Studies on Organic Fluorine Compounds. XII. Photolysis of (Fluoroalkyl)-s-triazines
- Studies on Organic Fluorine Compounds. XI. Reaction of Arylfluorophosphoranes with Alcohols
- Studies on Organic Fluorine Compounds. XLII. Synthesis and Reactions of Phenyltrifluoromethylacetylenes
- Studies on Organic Fluorine Compounds. XXII. Synthesis and Reactions of (Trifluoromethyl) benzofurans
- Studies on Organic Fluorine Compounds. XVIII. On the Mechanism of the Conversion of Trifluoromethyl Group to Amino Group on a Quinoline Ring
- Studies on Organic Fluorine Compounds. XVII. Reaction of Benzotrifluoride Derivatives with Sodium Amide
- Studies on the Reactions of Heterocyclic Compounds. XIII. Basicity of 1,6-Naphthyridine and Its N-Oxides : Correlation to Peracid Oxidation
- Studies on the Reaction of Heterocyclic Compounds. XII. N-Oxidation of Diazabenzene and Diazanaphthalene
- Photolysis of 2-(Trifluoromethyl) quinoline 1-Oxides and 1-(Trifluoromethyl) isoquinoline 2-Oxide
- Synthese von Derivaten der Cinchona-Alkaloide. XXXIII. Synthese von 2'-Cyanoderivaten der Alkaloide der Chinin-Reihe
- Synthetic Study of Amino-sugars from Pyridines. IV. Synthesis of 5-Amino-5-deoxypiperidinoses from the Singlet Oxygen Adduct of 1-Acyl-1,2-dihydropyridines. (1)
- Vittatolic Acid, a New Depsidone Isolated from the Lichen Hypogymnia vittata (ACH.) GAS.
- Studies on the Reactions of Heterocyclic Compounds. X. 1,3-Dipolar Cycloaddition Reaction of Isoquinolinium Ylides and Dicyanoacetylene
- Studies on the Reactions of Heterocyclic Compounds. IX. Syntheses of 1,10b-Dihydropyrrolo[2,1-α]isoquinolines and 2,3-Dihydropyrrolo[2,1-α]isoquinolines
- Studies on the Reactions of Heterocyclic Compounds. VI. 1,3-Dipolar Cycloaddition Reaction of Disubstituted Methylides of Isoquinoline and Pyridine with Acetylenic Compounds
- Studies on Transfer Ribonucleic Acids and Related Compounds. XXXIX. Chemical Synthesis of Heptadeca- and Hexadecaribonucleotides corresponding to the 3'-Terminus of the tRNA^_f of E. coli
- Studies on Transfer Ribonucleic Acids and Related Compounds. X. Synthesis of the Yeast Tyrosine tRNA 5'-Terminal Oligonucleotides
- Studies on the Reactions of Heterocyclic Compounds. VIII. 1,3-Dipolar Cycloaddition Reaction of Isoquinolinium Cyano (methoxycarbonyl)-methylide with Dimethyl Acetylenedicarboxylate : Structure and Reaction of the Adduct
- STEREOSELECTIVE SYNTHESIS OF gem-BISTRIFLUOROMETHYLCYCLOPROPANE DERIVATIVES
- Studies on Organic Fluorine Compounds. XXXI. Oxidative Coupling of Ketone Enolates and Trimethylsilyl Enol Ethers by Means of Cu(OTf)_2
- Studies on Organic Fluorine Compounds. IV. Conversion of Alcohols to Fluorides by Diphenyltrifluorophosphorane
- Studies on Organic Fluorine Compounds. III. Conversion of Alcohols to Fluorides by Difluorotriphenylphosphorane
- Studies on Organic Fluorine Compounds. LIV. : Synthesis of 2,2-Difluoroarachidonic Acid
- Studies on Organic Fluorine Compounds. XXXIX. Studies on Steroids. LXXIX. Synthesis of 1α, 25-Dihydroxy-26,26,26,27,27,27-hexafluorovitamin D_3
- Studies on the Reactions of Heterocyclic Compounds. XI. Methylation of Heteroaromatic N-Oxides
- Oxidative Cyanation of Aromatic Amine Oxides
- Studies on the Reactions of Heterocyclic Compounds. III. Cyanation of 1,6-Naphthyridine N-Oxides
- Studies on the Reactions of Heterocyclic Compounds. I. Syntheses and Some Reactions of 1,6-Naphthyridine N-Oxides
- Studies on the Reactions of Heterocyclic Compounds. V. Syntheses of Diazinium Ylides and Their Conversion to Azaindolizines
- Studies on the Reactions of Heterocyclic Compounds. IV. Preparations and Reactions of Heterocyclic N-Ylides
- 7.規那塩基の変換
- Studies on Organic Fluorine Compounds. X. Reaction of Trifluoromethyl Group in Heterocycles with Sodium Amide
- 1-PHENYLSULFONYL-3,3,3-TRIFLUOROPROPENE I : THE MICHAEL-TYPE ADDITION REACTION
- Studies on the Reactions of Heterocyclic Compounds. II. Syntheses and Some Reactions of 1,6-Phenanthroline N-Oxides
- Studies on organic fluorine compounds.-1,2-
- Synthese von Derivaten der Cinchona-Alkaloide. XXX. Ableitung einer Verbindung mit dem Tetrahydro-β-carbolin-Ring aus Chinin.
- Synthese von Derivaten der Cinchona-Alkaloide. XXIX. Uber Dihydroepinichin und seine Acylwanderung.
- Ableitung einer Verbindung mit dem Tetrahydro-β-carbolin-Ring aus Chinin
- Synthese von Derivaten der Cinchona-Alkaloide. XXVIII. Synthese von 2'-Hydroxydihydronichin.
- Studies on the Organic Fluorine Compounds. IX. Reactions of (Trifluoromethyl) quinolines with Metal Hydrides
- Studies on Organic Fluorine Compounds. VIII. Alcoholysis of (Trifluoromethyl) quinolines
- Studies on Organic Fluorine Compounds. VI. Preparations and Reactions of (Trifluoromethyl) quinoline N-Oxides
- Studies on Organic Fluorine Compounds. XXX. Ring Opening Reaction of Acetoxydifluorocyclopropanes with Various Nucleophiles
- Studies on Organic Flourine Compounds. V. Preparations and Reactions of N-Oxides of Trifluoromethylated Pyridines
- SYNTHESES OF β, β-DIFLUOROCARBOXYLIC ACID DERIVATIVES THROUGH THE CLAISEN REARRANGEMENT OF 1,1-DIFLUORO-1-ALKEN-3-OLS