[4,5-Dimethoxy-α-(3,4-dimethoxyphenyl)-o-tolyl]acetonitrile : A By-Product from the Reaction of 3,4-Dimethoxybenzyl Chloride with Sodium Cyanide
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概要
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The formation of [4,5-dimethoxy-α-(3,4-dimethoxyphenyl)-o-tolyl] acetonitrile (IV) as a by-product in the metathesis of 3,4-dimethoxybenzyl chloride (II) with sodium cyanide in dimethyl sulfoxide or N, N-dimethylformamide is reported. The structure of IV has been established by analysis, ultraviolet spectrum, infrared spectrum, nuclear magnetic resonance spectrum, and conversion into 4,5-dimethoxy-2-(3,4-dimethoxybenzyl)-N, N-dimethylphenethylamine (XI) through [4,5-dimethoxy-α-(3,4-dimethoxphenyl)-o-tolyl]acetic acid (VII) and 2-[4,5-dimethoxy-α-(3,4-dimethoxyphenyl)-o-tolyl]-N, N-dimethylacetamide (VIII). The sample of XI thus obtained was identical with the one produced by catalytic hydrogenolysis of 1-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2,2-dimethylisoquinolinium chloride, which was synthesized from 1-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline (IX) by quaternization with methyl iodide and treatment of the resulting methiodide (X) with silver chloride. The reaction of benzyl chloride with sodium cyanide in dipolar aprotic solvents was found to give a small amount of 2,3-diphenylpropionitrile (XIV) besides benzyl cyanide.
- 公益社団法人日本薬学会の論文
- 1971-07-25
著者
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藤井 澄三
Faculty Of Pharmaceutical Sciences Kanazawa University
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三口 守公
Research Center Taisho Pharmaceutical Co. Ltd.
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上野 幸子
Faculty Of Pharmaceutical Sciences Kanazawa University
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三口 守公
Faculty of Pharmaceutical Sciences, Kanazawa University
関連論文
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- Purines. LXIX. Direct N(1)-Oxidation of 7-Benzyladenine and Stepwise Syntheses of Its N(1)- and N(3)-Oxides
- Purines. LXVIII. Trifluoroperoxyacetic Acid Oxidation of N^6-Benzyladenine : Formation of the N(3)-Oxide and N(7)-Oxide, and Their Cytokinin Activities
- Purines. LXVII. An Alternative Synthesis of Adenine 7-Oxide : N-Oxidation of the Adenine Ring Utilizing Blocking/Deblocking at the 1-Position
- Purines. LXVI. Adenine 7-Oxide : Its Synthesis, Chemical Properties, and X-ray Molecular Structure
- Purines. LII. Synthesis and Biological Evaluation of 8-Methylguanine 7-Oxide and Its 9-Arylmethyl Derivatives
- Purines. LI. Synthesis and Biological Activity of Hypoxanthine 7-N-Oxide and Related Compounds
- Purines. L. Synthesis and Antileukemic Activity of the Antibiotic Guanine 7-Oxide and Its 9-Substituted Derivatives
- Purines. LX. Dimroth Rearrangement and Concomitant Hydrolytic Deamination of 7-Alkyl-1-methyladenines
- Lactams. VII. Stereochemical Characterization and Cis-Trans Isomerization of 5-Ethyl-2-oxo-4-piperidineacetic Acid and Related Compounds
- Lactams. XVII. Synthesis and Stereochemical Characterization of Diethyl cis-and trans-5-Ethyl-2-oxo-4-piperidinemalonate
- Quinolizidines. XXVI. : A Synthesis of (±)-Deplancheine
- Purines. XLI. : An Alternative Synthesis and the Chemical Behavior of 7,9-Dialkyladeninium Salts
- Purines. XXXVIII. A General Synthesis of 7,9-Dialkyladeninium Salts from 9-Alkyladenines by Regioselective Alkylation : Utilization of an N^6-Alkoxy Group as a Control Synthon
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- Lactams. VIII. The Alkaline Ferricyanide Oxidation of 3-Substituted 1-(3,4-Dimethoxyphenethyl) pyridinium Salts : Effects of Hydrocarbon Substituents on Orientation of the Oxidation
- Lactams. VI. Synthesis and Nuclear Magnetic Resonance Study of 1-Aralkyl-3-methyl- and -5-methyl-2(1H)-pyridones
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- Purines. LV. Syntheses and cytokinin activities of some adenine and adenosine derivatives related to 1'-methylzeatin
- Pourines. XLV. : Syntheses and Cytokinin Activities of the Cis Isomers of (1'R)-1'-Methylzeatin and Its 9-β-D-Ribofuranoside
- Purines. XXXV. : Synthesis and Cytokinin Activity of Racemic 1'-Methylzeatin
- Purines. XXXIII. Syntheses and Cytokinin Activities of Both Enantiomers of 1'-Methylzeatin and Their 9-β-D-Ribofuranosides
- フリニルアミノ酸,フリニルヘフタイトおよび関連化合物のサイトカイニン活性について(A. 理学)
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- Purines. LVIII. A Synthesis of 7-Alkyl-1-methyladenines from Adenosine by Regioselective Alkylation : Uilization of a 1-Methoxy Group as a Control Synthon
- Purines. LVII. Regioselective Alkylation of N^6,9-Disubstituted 8-Oxoadenines : Syntheses of the Sea Anemone Purine Caissarone and Some Positional Isomers and Analogues
- Purines. LIV. Intramolecular Cyclization of 9-Ethyl-1-(2-hydroxyethyl)adenine Caused by Nucleophiles : Formation of N^6,1-Ethanoadenine Derivatives
- Purines. LIII. Deamination of 1-(ω-Hydroxyalkyl)adenine Derivatives by Nucleophiles
- Purines. XLIX. Synthesis and Proton Nuclear Magnetic Resonance Study of 3,7-Dialkylxanthines and 1,3,7-Trialkylxanthines
- Purines. XLVIII. Syntheses and Proton Nuclear Magnetic Resonance Study of 2-Deuterioadenines Substituted or Unsubstituted at the 9-Position and of Their N-Oxygenated Derivatives
- Purines. XLVI. Preparation of 1-Ethyladenine from Adenosine
- Quinolizidines. XX. Racetnic and Chiral Syntheses of the Alangium Alkaloids 9-Demethylprotoemetinol and 10-Demethylprotoemetinol(Organic,Chemical)
- Lactams. XXVI. Regioselectivity in the mercuric acetate- edetic acid oxidation of the ethyl 1-(2-aryl-2-hydroxyethyl)-3- ethyl-4-piperidineacetate system: Enhancement by a benzyloxy group in the aryl moiety and by the 3,4-cis configuration
- Quinolizidines. XXV. : An Extension of the "Lactim Ether Route" to the Racemic Syntheses of Several Indolo[2,3-α]quinolizidine Alkaloids
- Quinolizidines. XVIII. Synthesis of (-)- and (+)-ankorines through a lactim ether route
- Quinolizidines. XIII. Syntheses of (±)-and (-)-Alangimarckines
- Lactams. XXIII. Thermal cis-trans isomerization of the 5-ethyl-2-oxo-4-piperidineacetic acid system: Effect of an N-substituent
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- Synthesis of 5-(Alkylamino)-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamides : Key Intermediates for the Synthesis of 3-Alkyl-9-β-D-ribofuranosylpurine Derivatives
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- Purines. XXV. Fission and Reclosure of the Adenine Ring by the Use of Modified Benzyloxy Groups at the 1-Position
- Purines. XX. Synthesis of 1-Substituted 5-Aminoimidazole-4-carboxamidines and Related Compounds
- Purines. XIV. Selective Removal of N-Terminal Amino Acids from Peptides by the Use of Purin-6-yl Group at the N-Terminus
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- Purines. XLVII. Dimroth Rearrangement versus Hydrolytic Deamination of 1-Ethyladenine
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- Quinolizidines. XXVIII. Racemic and chiral syntheses of ochromianine, an indoloquinolizidine alkaloid from Neisosperma miana
- Quinolizidines. XXVII. Racemic and chiral syntheses of the Neisosperma and Ochrosia alkaloid ochropposinine
- Quinolizidines. XXIV. : Syntheses of Ankorine Congeners in Different Oxidation States
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- Quinolizidines. XIV. A racemic synthesis of 9-demethyltubulosine, an alkaloid isolated from Alangium vitiense
- Purines. XLIV. : A Kinetic Study of the Dimroth Rearrangement of the Marine Sponge Purine 1,9-Dimethyl-8-oxoadenine and Related Compounds
- Purines. XLIII. : A Total Synthesis of the Marine Sponge Base 6-Imino-1,9-dimethyl-8-oxopurine
- Lactams. XV. Chemistry of Unsaturated δ-Valerolactams
- Lactams. XVIII. Oxidation of 1-Substituted 3-tert-Butyl-piperidine with Mercuric Acetate-EDTA
- Lactams. XIX. The Alkaline Ferricyanide Oxidation of 1,3-Disubstituted Pyridinium Salts : Effects of Branched Alkyl Groups at the 3-Position
- Synthesis of 3-tert-Butylpyridine
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- Purines. XL. : Preparation of 9-(ω-Carboxyalkyl)-3-methyladenines
- The Preparation of 3,4-Dimethoxy-and 3,4-Methylenedioxy-Phenethyl Alcohol
- Purines. XXXVI. : Fission and Reclosure of the Adenine Ring in 3,9-Disubstituted Adenines : Effects of Substituents
- Purines. XXXIV. : 3-Methyladenosine and 3-Methyl-2'-deoxyadenosine : Their Synthesis, Glycosidic Hydrolysis, and Ring Fission
- A General and Convenient Synthesis of 7-Alkyladenines from Adenine by Regioselective Alkylation Utilizing Blocking/Deblocking at the 3-Position
- Purines. XXVII. : Hydrolytic Deamination versus Dimroth Rearrangement in the 9-Substituted Adenine Ring : Effect of an ω-Hydroxyalkyl Group at the 1-Position
- Purines. XXVI. The Dimroth Rearrangement of 9-Substituted 1-Methyladenines : Accelerating Effect of a β-D-Ribofuranosyl Group at the 9-Position
- Purines. XXIV. Methylation of N^6-Alkoxyadenines and N^6-Methyladenine
- Purines. XIII. Ring Opening of 3-Alkyladenines with Carbobenzoxy Chloride : Transformation into 8-Hydroxylated Adenines
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- Debenzylation of N-Benzyl-acylamides.
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- Quinolizidines. II. A Stereoselective Synthesis of Emetine
- Preparation of Some Ring-Oxygenated Phenacyl Bromides
- Lactams. XIV. cis-trans Isomerization in the 5-Ethyl-2-oxo-4-piperidineacetic Acid System under Fischer-Speier Esterification Conditions
- Lactams. XII. Improvements in the Synthesis of Ethyl trans-5-Ethyl-2-oxo-4-piperidineacetate
- Lactams. XI. Construction of Lactam Carbonyl Function in 1,3-Disubstituted Piperidines by Mercuric Acetate-EDTA Oxidation : Effects of Carbonyl and Related Groups at the 3-Position
- Lactams. IX. Generation of Lactam Carbonyl Function in 1,3-Disubstituted Piperidines by Mercuric Acetate-EDTA Oxidation : Effects of Hydrocarbon Substituents at the 3-Position