Studies on Pyrimidine Derivatives and Their Related Compounds. LXXVIII. Unusual Reactions of Thiamine Free Base with Some Electrophilic Reagents

スポンサーリンク

概要

• 論文の詳細を見る

• Reaction of thiamine free base (I) with ethyl pyrocarbonate afforded the 1 : 1 adduct (VIII) which was hydrolyzed to IX via N-C bond cleavage of pyrimidopyrimidine nucleus of I. The reaction of I with ethyl chloroformate also afforded VIII, together with IX. On the other hand, the reaction of I with benzoyl chloride yielded dibenzoate (IV) as the major product and monobenzoate (V) as the minor product, these compound being analogues of IX. The mechanisms of these reactions are discussed as shown in Chart 2.

• 公益社団法人日本薬学会の論文
• 1973-04-25

著者

• 高見沢 映

  新潟薬科大学

• 牧野 逸男

  塩野義製薬株式会社研究所

• 牧野 逸男

  Shionogi Research Laboratory, Shionogi & Co., Ltd.

• 牧野 逸男

  塩野義製薬研究所

• 高見沢 映

  Shionogi Research Laboratory Shionogi & Co. Ltd.

• 米沢 純子

  Shionogi Research Laboratory, Shionogi & Co., Ltd.

• 米沢 純子

  Shionogi Research Laboratory Shionogi & Co. Ltd.

関連論文

• Studies on Pyrimidine Derivatives and Related Compounds. LXXV. Reactions of Thiazolium Salts with Diethyl Acylphosphonates and Hydroxylation of Some 3-Oxo-2,3-dihydro-4H-1,4-thiazine Derivatives
• Studies on Pyrimidine Derivatives and Related Compounds. XLVII. Reaction of Thiamine with Dialkyl Acylphos-phonates or Methyl Phenylacyl-phosphinates : Takamizawa Reaction 6
• Studies on Pyrimidine Derivatives and Related Compounds. XLVI. The Reactions of Diethyl Acetylphosphonate with Thiamine : Takamizawa Reaction (5).
• Studies on the Pyrimidine Derivatives and Related Compounds. XL. Reaction of 3-Benzyl-4-methyl-5-(2-hydroxyethyl)thiazolium Salts with Diethyl Benzoylphosphonate
• Studies on the Pyrimidine Derivatives and Related Compounds. XXXIX. On the Oxidation Products of 2-Pheny1-4-(2-methyl-4-amino-5-pyrimidyl)methyl-5-methyl-6-(2-benzoyloxy or hydroxy)-ethyl-4H-1,4-thiazin-3(2H)-one
• 14.ビタミンB_1関連チアゾール誘導体とDiethylbenzoylphosphonateとの反応(第155回会議研究発表要旨)
• Studies on the Pyrimidine Derivatives. XXVII. A New Method for Synthesis of Diethyl Ethoxycarbonylphosphite from Tris (ethoxythiocarbonyl) Phosphorotrithioite, and on the Reactions of these Organo-phosphorus Compounds with Thiamine Sodium Salt.
• Studies on Pyrimidine Derivatives and Related Compounds. LIII. The Reaction of Thiamine with Diethyl Acetylphosphonate (Supplement) and the Synthesis of Pseudothiamine
• Studies on Pyrimidine Derivatives and Related Compounds. LII. Reaction of Thiamine with Phosphites. (1)
• Studies on the Pyrimidine Derivatives and Related Compounds. XXXV. On the Reaction Product of Thiamine with Diethyl Benzoylphosphonate
• チアミン遊離塩基と臭化シアンあるいは過酸化水素との反応
• 6.Thiamine Free BaseとBrCNとの反応(ビタミンB研究委員会 : 第244回会議研究発表要旨)
• Studies on Pyrimidine Derivatives and Related Compounds. XCIV. On the Oxidation Products of 2-Substituted-2,3-dihydro-4H-1,4-thiazin-3-one Derivatives. (2)
• On the Reaction of Dialkyl Acylphosphonate with 2-Methyl-1,3,4-thiadiazolium Salts
• On the Reaction of Dialkyl Acylphosphonate with 2-Methylthiazolium Salts
• On the Reactions of 1,3,4-Oxadiazolium Salts with Dialkyl Acylphosphonates. A Novel Synthesis of 1,3,4-Oxadiazin-5-one Derivatives
• Pyrimidine誘導体及び関連化合物の研究(第89報) : ビタミンB_1とジエチルアシルホスホネートとの反応
• Studies on Pyrimidine Derivatives and Related Compounds. LXXXVII. Reaction of Thiamine Analogues with Diethyl Benzoylphosphonate
• On the Reactions of Oxazolium Salts with Dialkyl Acylphosphonates. A Novel Synthesis of 1,4-Oxazin-3-one and Azetidin-2-one Derivatives
• Studies on Pyrimidine Derivatives and Related Compounds. LXXVII. Reaction of Thiamine Analogues with Diethyl Benzoylphosphonate
• Studies on Pyrimidine Derivatives and Related Compounds. LXXIII. Syntheses and Reactions of Thiamine Sulfur Analogues and Related Derivatives. (2)
• Studies on Pyrimidine Derivatives and Related Compounds. LXXII. Syntheses and Reactions of Thiamine Sulfur Analogues and Related Derivatives. (1)
• Studies on Pyrimidine Derivatives and Related Compounds. LXXI. Reaction of Thiamine Anhydride with Thiols
• Studies on Pyrimidine Derivatives and Related Compounds. LXX. A Novel Reaction of Thiamine Anhydride
• Studies on Pyrimidine Derivatives and Related Compounds. LXIX. Sythesis of Thiamine Free Base
• Studies on Pyrimidine Derivatives and Related Compounds. LXVIII. Reactions of Dialkyl Acylphosphonates with 1,3-Disubstituted Benzimidazolium Halides
• Studies on Pyrimidine Derivatives and Related Compounds. LXVII. Reaction of Thiadiazolium Derivatives with Dialkyl Acylphosphonates
• Studies on Pyrimidine Derivatives and Related Compounds. LXVI. Reactions of Dialkyl Acylphosphonates with 1,3,4-Thiadiazolium Derivatives
• Investigation on the Reaction of Benzazolium Salts with Base
• Studies on Pyrimidine Derivatives and Related Compounds. LIX. Syntheses of 2,3-Dihydro-1H-pyrazolo [5,1-b] purin-2-ones
• 7.Triethylammonium 2[4-(4-amino-2-methyl-5-pyrimidinyl)methyl-3-methyl-6-phenyl-5-oxo-5,6-dihydro-4H-1,4-thiazin-2-yl]ethyl pyrophosphateの合成(ビタミンB研究委員会 : 第224回会議研究発表要旨)
• 6.ThiamineとDiethyl acylphosphonateの反応補遺(ビタミンB研究委員会 : 第224回会議研究発表要旨)
• 3. 2-ハロチアゾリウム塩を用いるジチオカルバミン酸塩の活性化 : ビタミンB研究委員会第262回会議研究発表要旨
• Studies on the Urinary Metabolites of Isophosphamide and Its Activated Species in Rabbits
• Synthesis, Stereochemistry and Antitumor Activity of 4-Hydroperoxyiso-phosphamide (NSC-227114) and Related Compounds
• Syntheses of New Cyclophosphamide Derivatives Having 1,3,4,2-Oxadiazaphosphorinane and Related heterocyclic Systems
• Addition Reaction of 3-Substituted-4-methyl-5- (2-hydroxy) ethyl-thiazolium Salt with Diaryl Carbodiimide
• Studies on Pyrimidine Derivatives and Related Compounds. LXXXI. Reactions of Aryl Isothiocyanates with Thiamine and Related Thiazolium Ylides
• Studies on Pyrimidine Derivatives and Related Compounds. LXII. Cycloadditions of Alkyl Isothiocyanates with Thiamine and Related Thiazolium Ylids and Facile Conversions of the Adducts to Dihydroimidazo [4,5-d] thiazole Derivatives
• Studies on Pyrimidine Derivatives and Related Compounds. LX. Synthesis of Hydroxymethylthiamine
• Studies on Pyrimidine Derivatives and Related Compounds. LIV. Reactions of Thiamine with α-Ketoaldehydes
• 23.ピリミジン誘導体および関連化合物の研究 : (LXIV補遺)ビタミンB_1とアルデヒドの反応(5)(一般研究発表要旨)
• ビタミンB研究委員会第230回会議研究発表要旨
• 7.O-Tetrahydropyranyl-S-alkoxycar-bonylthiamineの製法について(第143回会議研究発表要旨)
• 13.アクリロニトリルより2-Methyl-4-amino-5-acetaminomethylpyrimidineを合成する場合の中間体について(第84回協議会研究発表要旨)
• Studies on Pyrimidine Derivatives and Related Compounds. XLIX. Several Reactions of 1-[(2-Methyl-4-amino-5-pyrimidinyl) methyl]-3-alkyl-4-(2-hydroxyethyl)-5-methyl-imidazolium Salts.
• Studies on Pyrimidine Derivatives and Related Compounds. XLIV. Syntheses of Thiazolo [3,2-a] pyrimidine Derivatives
• Studies on Pyrimidine Derivatives and Their Related Compounds. XCI. On the Oxidation Products of 2-Substituted-1,4-thiazin-3-one Derivatives
• チアミン遊離塩基(Thiamine Free Base)とDiethyl Pyrocarbonate及びEthyl Chloroformateとの反応
• 5.Thiamine Free Baseの立体構造(ビタミンB研究委員会 : 第241回会議研究発表要旨)
• 1.Thiamine Free BaseとDiethyl pyrocarbonate及びEthyl chlorocarbonateとの反応(その2)(ビタミンB研究委員会 : 第239回会議研究発表要旨)
• 2-2.Thiamine Free Baseの酸化について(ビタミンB研究委員会 : 第235回会議研究発表要旨)
• 2-1.2-Substituted-4-(2-methyl-4-amino-pyrimidine-5-yl)methyl-5-methyl-6-(2-hydroxy)ethyl-4H-1,-thiazine-3(2H)-oneとH_2O_2との反応補遺(ビタミンB研究委員会 : 第235回会議研究発表要旨)
• 1.2-Substituted-4-(2-methyl-4-amino-pyrimidin-5-yl)一methyl-5-methyl-6-(2-hydroxy)ethyl-4H-1,4-thiazine-3(2H)-oneとH_2O_2との反応 : (ビタミンB研究委員会 : 第230回会議研究発表要旨)
• Studies on Pyrimidine Derivatives and Their Related Compounds. LXXXVI. Unusual Reactions of Thiamine Derivatives
• Synthese of 4-Aryliminoparabanic Acids and 2-Arylimino-2,3-dihydro-1,4-thiazine Derivatives via 2-N, N'-Diarylamidinothiazolium Salts
• Studies on Pyrimidine Derivatives and Related Compounds. LXXX. Unusual Reactions of Thiamine Free Base with Electrophilic Reagents. (2)
• Studies on Pyrimidine Derivatives and Their Related Compounds. LXXVIII. Unusual Reactions of Thiamine Free Base with Some Electrophilic Reagents
• 1.α-ケトアルデヒドのThiamineおよびHydride acceptorによる酸化 : (α-ケトアルデヒド代謝におけるThiamineの新しい役割に対する化学的モデル)(THE JOURNAL OF VITAMINOLOGY : 掲載論文要旨)
• 14.ピリミジン誘導体および関連化合物の研究(第94報)α-Ketoaldehyde付加チアミン誘導体のHydride acceptorにたいする挙動(日本ビタミン学会 : 第22回大会研究発表要旨)
• Studies on Pyrimidine Derivatives and Related Compounds. XLV. On Some Synthetic Methods of N-[1-(2-Oxo-1,3-oxathian-4-ylidene) ethyl]-N-[(2-methyl-4-amino-5-pyrimidinyl)-methyl] formamide
• Studies on 1,3-Dithiolium Cations. III. Stability and Electronic Structure of 4-p-Substituted Phenyl Derivatives
• Studies on Pyrimidine Derivatives and Related Compounds. LXV. On the Reactions of Thiamine with Carbon Disulfide
• Studies on 1,3-Dithiolium Cations. II. Reactions of 4-Phenyl Derivatives with Nucleophilic Reagents
• Studies on 1,3-Dithiolium Cations. I. A Novel Synthetic Method of 4-p-Substituted Phenyl Derivatives and Related Compounds
• Studies on Pyrimidine Derivatives and Related Compounds. LVI. Reaction of Thiamine with Isocyanates. (I)
• Studies on Pyrimidine Derivatives and Related Compounds. LI. Reaction of Thiamine with Amines. (1)
• Studies on Pyrimidine Derivatives and Related Compounds. L. Reactions of Thiamine with Aldehydes
• Synthesis of 4-Hydroperoxy-1,3,2-diazaphosphorinane-2-oxides related to the Activated Cyclophosphamide
• Studies on Pyrimidine Derivatives and Related Compounds. LXXXIII. An Unusual Reaction of Thiamine Ylide with Diaryl Carbodiimide
• An Unusual Heterocyclic Transformation in Liquid Ammonia
• 1.ビタミンB_1とDi-p-tolylcarbodiimideとの反応(第185回会議研究発表要旨)
• Camphane Derivatives. VII. Syntheses and Structure of 3-Methyl-3aβ, 7aβ-bornano[3,2-d]oxazolidin-2-one and its Derivatives
• Nuclear Magnetic Resonance Studies of Bridged Ring Systems. V. Signals of Methyl Groups in Bornane Derivatives
• Isolation of cis-and trans-2-Methoxymethylene-3-ethoxypropionitrile
• Studies on the Pyrimidine Derivatives and the Related Compounds. XXXVIII. Investigation on 2-Alkoxy-methylene-3-ethoxypropionitrile and Ethyl 2-Alkoxymethylene-3-ethoxypropionate
• 16.Hydroxymethylthiamineの合成(第176回会議研究発表要旨)
• Studies on the Pyrimidine Derivatives. XXX. Syntheses and Reactions of O-(2-Tetrahydropyranyl)-thiamine, O-Tritylthiamine, S-Acylthiamine, and S-Alkoxycarbonylthiamine.
• Syntheses of Pyrazole Derivatives. XI. Acetylation Products of 7-Aminopyrazolo [1,5-a] pyrimidines. Supplement
• Syntheses of Pyrazole Derivatives. IX. Acetylation Products of 7-Aminopyrazolo [1,5-α] pyrimidines
• Studies on the Pyrimidine Derivatives. XXIV. Syntheses of Several Thiol-type Thiamine Derivatives and their Primary Screening Tests.
• Studies on the Pyrimidine Derivatives. XXII. The Syntheses of New Thiamine Derivatives.
• Oxidation of α-Ketoaldehyde by Thiamine and Hydride Acceptor:A Chemical Model for a New Role of Thiamine in the α-Ketoaldehyde Metabolism
• SYNTHESES OF O, S-DICHOLANOYL-THIAMINE DERIVATIVES
• Studies on the Pyrimidine Derivatives. XXI. On the Studies of S-Alkoxycarbonylthiamine. (2).

もっと見る 閉じる

スポンサーリンク