Studies on Pyrimidine Derivatives and Related Compounds. LXXX. Unusual Reactions of Thiamine Free Base with Electrophilic Reagents. (2)
スポンサーリンク
概要
- 論文の詳細を見る
The reaction of thiamine free base (I) with isocyanate derivatives in polar solvent such as dimethylformamide afforded 2- (7-methyl-3,4-dihydropyrimido [4,5-d] pyrimidin-3-yl) -2-methyltetrahydrofuran-3-yl alkyl (aryl) carbamthiolate (V), which then reacted with another isocyanate molecule to give N-carbamoylthiamine free base (II). The reaction mechanism is discussed kinetically. The reaction of I with isocyanate derivatives in less polar solvent such as chloroform afforded only II-analogues. The reaction of II with N, N-disubstituted carbamoylchlorides afforded 2- [N-formyl-N- (2-methyl-4-aminopyrimidin-5-yl) methyl] amino-2-methyltetrahydrofuran-3-yl disubstituted carbamthiolates (VIIa-c).
- 公益社団法人日本薬学会の論文
- 1974-02-25
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).