Reaction of 1-Arylbiguanide with Some Carboxylic Esters.

スポンサーリンク

概要

• 論文の詳細を見る

• The reaction of arylbiguanide with carboxylic esters having a reactive functional group except the ester group such as ethyl cyanoacetate, ethyl acetoacetate and diethyl oxalate was attempted. Roy et al. inferred that the reaction product of arylbiguanide with ethyl cyanoacetate should be 2-arylguanidino-6-amino-4-pyrimidinol. Contrary to the Roy's result, however, the author proved that it might be 4-amino-6-arylamino-s-triazine-2-acetonitrile. In comparison with this fact, the reaction of 1-arylbiguanide with ethyl acetoacetate was confirmed to afford 2-arylguanidino-6-methyl-4-pyrimidinol under the similar reaction condition. Furthormore, the author defined the reaction mechanism in which 1-arylbiguanide reacts with diethyl oxalate to give ethyl 4-amino-6-arylamino-s-triazine-2-carboxylate through the intermediate formation of 1-aryl-3-(4,5-dioxo-2-imidazolidinylidene)-guanidine. In connection with this finding, 4-amino-6-(p-toluidino)-s-triazine-2-carboxamide derivatives was found to be formed by the reaction of 1-(p-tolyl)-3-(4,5-dioxo-2-imidazolidinylidene)-guanidine with corresponding amine. Therefore it is recommended to be a new method of synthesizing 4-amino-6-arylamino-s-triazine-2-carboxamides from 1-arylbiguanide, diethyl oxalate and an amine.

• 公益社団法人日本薬学会の論文
• 1962-12-25

著者

• 古川 潮

  Faculty Of Pharmaceutical Sciences Kumamoto University

• 古川 潮

  Pharmaceutical Instiute, Keio-Gijuku University

関連論文

• Studies on Antitumor Substances. XIV. Syntheses of Bisquarternary Ammonium Salts and the Reaction with Nucleophiles
• Studies on Antitumor Substances. VII. Reaction of N-Amidino-O-alkylisourea with Some Carboxylic Esters
• The Mechanism for the Reaction of Biguanides with Diethyl Oxalate
• Syntheses of New Pyrazoline Derivatives
• Studies on Antitumor Substances. VI. Chemical Behaviors of Thiosulfonates, Disulfonyl Sulfides, and Related Compounds.
• Studies on Antitumor Substances. V. Reaction of Thiosulfonates with Active Methylene Compounds.
• Facile Reduction of Intermediates from Carboxylic Acids and 6-Nitro-1-(2-nitrophenylsulfonyloxy)benzotriazole with Sodium Borohydride to Alcohols
• The Reaction of 1,3-Disubstituted Thioureas with α, ω-Dibromoacyl Chlorides and the Formation of Spiro Compounds
• Reactions of p-Toluenesulfinic Acid with Dialkoxy or Diamino Sulfides and Disulfides
• A Facile Preparation of 4-Thiazolone Derivatives from Thioamides and Various Haloacyl Halides in a Biphase System
• Facile Preparations of 1,4-(Diphenylmethyleneamino) piperazine-2,5-diones and N-Phenylmethyleneamino-β, γ, and δ-lactams from Benzylidene Hydrazines and α, β, γ, and δ-Haloacyl Halides
• Reaction of Biguanides and Related Compounds. XV. Cyclizations of Arylbiguanides and 2-Guanidinobenzimidazole with Bifunctional Unsaturated Dicarboxylates to s-Triazines and Imidazolines
• Behavior of Sulfinic Acid toward N-Chloramines and Related Compounds
• Facile Formation of 1,3-Disubstituted 2,3,5,6-Tetrahydro-2-thioxopyrimidin-4 (1H)-ones and 2-N, 3-Disubstituted 2,3,5,6-Tetrahyro-2-imino-1,3-thiazin-4-ones from Thioureas and β-Haloacyl Halides
• Convenient One-pot Syntheses of Sulfinates, Sulfinamides, and Thiosulfinates by Sulfinylation with p-Toluenesulfinic Acid and Activating Reagents
• A One-Pot Synthesis of β-Lactams by the Reaction of β-Haloacyl Chlorides with α-Amino Acids
• Convenient Syntheses of Cyclic Carboxamides from α, β, γ, δ and ε-Halocarboxamides under Phase Transfer Conditions
• Direct Conversion of Sulfinic Acid to Sulfonic Acid Derivatives
• Thermal Dimerization of Sulfinyl Compounds
• Novel One-step Preparation of Sulfinic Acid Derivatives from Sulfinic Acid
• Asymmetric Synthesis of β-Amino-α, α-dimethyl-β-phenylpropionic Acid. The Reactions of Chiral Schiff Bases with Dimethylketene and with Reformatsky Reagent
• Asymmetric Syntheses of β-Amino Acids by the Reduction of Enamines
• Reaction of Epoxides. VI. Reaction of 2,3-Epoxypropyl Aryl Ether with Ethyl-N-phenylformimidate and N, N'-Diphenylformamidine
• Reaction of Biguanides and Related Compounds. XIV. Cyclization of Amidinothioureas with Some Carbonyl Compounds
• Asymmetric Syntheses of β-Amino Acid and Aspartic Acid by Reformatsky Reaction
• Asymmetric Syntheses of β-Amino Acids by the Addition of Chiral Amines to C=C Double Bonds
• Behaviors of N-(Substituted thio) phthalimides, N-(Substituted thio)-succinimides, and N-(Substituted thio) isatins toward Some Nucleophiles
• Reaction of Biguanides and Related Compounds. XIII. Benzilic Acid Rearrangement. The Reactions of 1,2-Cyclohexanedione and 9,10-Phenanthrenequinone with Arylbiguanides and N-Amidino-0-alkylisoureas
• Conversion of Bis (β-carbamoylethyl) Disulfides into Bis (β-carbamoylethyl) Trisulfides
• Reaction of Biguanides and Related Compounds. XII. Condensations of Arylbiguanides and Amidinoisoureas with Isatins
• Pyrazolines and Oxazolines. Reaction of Arylcarbonylethylthiosulfates with Hydrazines and Hydroxylamines
• Reaction of Epoxides. V. 1,3-Dipolar Cycloaddition Reaction of Epoxides with Carbon-Nitrogen Double Bond Compounds
• Reaction of Biguanides and Related Compounds. X. Formation of s-Triazinethiones by the Condensation of Arylbiguanides with 2,3-Trithiocarbonates
• Thiation of Enamine of Cyclohexanone with Arensulfenamides
• Reaction of Biguanides and Related Compounds. IX. Condensation of N-Amidino-O-alkylisourea and 1-Substituted 3-Amidino-2-thiourea with Benzil
• Reaction of Biguanides and Related Compounds. VIII. The Condensation of Arylbiguanides and N-Amidino-O-alkylisoureas with Diketene and Ethyl Acetoacetate
• The Reaction of Benzyl Phenylmethanethiosulfinate with Amines
• Reaction of Epoxides. IV. Addition of 2,3-Epoxypropyl Phenyl Ether to Oximes and Hydrazones
• Criss-cross Cycloaddition of Epoxides to Aromatic Aldazines
• Arylthiation of Cyclohexanone Morpholine Enamine with Aryl Benzenethiosulfonates
• A Convenient Synthesis of Pyrazolines from β-Carbonylethylthiosulfates
• Reaction of Biguanides and Related Compounds. VII. The Condensation of Arylbiguanide with α, β-Unsaturated Carboxylic Ester in Dimethylformamide
• Reactions of β-Carbonylethylthiosulfates and β-Carbamoylethyl Disulfides with Amines
• Reaction of Biguanides and Related Compounds. VI. Condensation of N-Amidino-O-alkylisourea with β-Diketone
• Sulfenylation of Morpholine Enamine of Cyclohexanone with Sulfenamides and Thiosulfonates
• Mechanism for the Reaction of Sodium Benzylthiosulfate with Morpholine
• Antiviral Effect and Syntheses of 4-Amino-6-alkylamino-s-triazine-2-carboxylic Acid Derivatives. Researches on Chemotherapeutic Drugs against Viruses. XXXVI.
• Syntheses of Compounds related to Guanidine and their Inhibitory Action on Growth of HeLa Cells.
• Reaction of Epoxides. II. Synthesis of Oxazolidine by the Reaction of Epoxide with Schiff Base
• Studies on Antitumor Substances. XII. Synthesis of Bis (2,3-epoxypropyl) amine Derivatives and the Reaction with Some Nucleophiles
• Reactions of Epoxides. I. Synthesis of Trithiocarbonate by the Reaction of Epoxide with Alkali Xanthate
• Studies on Antitumor Substances. XI. Reactions of Bunte Salts with Nucleophiles
• Formation of Trisulfide from Thiosulfonate with Amine Catalyst
• Reaction of Disulfide and Trisulfide with N-Chlorocarboxamide
• Reaction of Biguanides and Related Compounds. III. Reaction of Biguanide and Amidinoisourea with Oxamate
• Reaction of Biguanides and Related Compounds. II. Reaction of Biguanides with Benzil
• Reaction of Biguanides and Related Compounds. I. Reaction of Biguanides with β-Diketone
• Studies on Antitumor Substances. XIII. Reaction of Sodium Ethoxycarbonylmethylthiosulfate and Sodium Phenacylthiosulfate with Amine
• Reaction of N-Amidinoamidine with Diethyl Oxalate and Ethyl Oxamate
• Studies on Application of Amino Acid as Medicinal Agent. II. Reaction of Amino Acid Ester with Difunctional Grignard Reagent
• Studies on Antitumor Substances. X. Reactions of Thiosulfonates with Some Nucleophilic Compounds
• Studies on Antitumor Substances. IX. Chemical Behaviors of Thiosulfonate toward Active Methylene Compound
• Studies on Antitumor Substances. VIII. Syntheses of 4-Amino-6-substituted Amino-2-substituted sym-Triazine Derivatives
• Studies on Application of Amino Acid as Medicinal Agent. I. Syntheses of Amino-tert-alcohol Derivatives
• Reaction of Epoxides. III. The Synthesis of 2-Amino-5-substituted 4,5-Dihydrothiophene from Substituted Propylene Sulfides and Ethyl Cyanoacetate
• Reaction of Biguanides and Related Compounds. V. The Base-catalyzed Condensation of Benzil with 1,1-Dialkylguanidine
• Reaction of Cyclic Trithiocarbonate with Amine and Phenylhydrazine
• Reaction of Biguanides and Related Compounds. IV. Reaction of Arylbiguanide with Benzoylacetone in the Presence of a Small Amount of the Arylbiguanide Hydrochloride
• A Stereoselective Synthesis of α-Chloro-α-phenylacetamide by the Reaction of optically Active Schiff Base with Dichlorocarbene
• The Conversion of α-Carbonylmethylthiosulfates into Thiocarboxamides
• Antitumor Effects of Pentamethylene Bismethanethiosulfonate Hydrolysates and Difunctional Bunte Salt
• Syntheses and Antiviral Effects of 3-Amino-6-alkyl-as-triazin-5-ol Derivatives.
• Syntheses of 4,6-Diamino-s-triazine-2-carboxamide Derivatives.
• Researches on Chemotherapeutic Drugs Against Viruses. XXXV. Syntheses and Antiviral Activity of Alkylated Ephedrine and its Related Compounds.
• Reaction of 1-Arylbiguanide with Some Carboxylic Esters.
• Studies on Syntheses of Dimethylated Ephedrine Derivatives.

もっと見る 閉じる

スポンサーリンク