Synthesis of 5,5'-Mehylenebispyrimidine Derivatives and 3,4-Dithia[6.1](1.5)pyrimidinophane

スポンサーリンク

概要

• 論文の詳細を見る

• Convenient syntheses of 3,6-dimethyl-1,3-oxazine-2,4(3H)-dione (3) and 5,5'-methylenebis[1-(2-hydroxyethyl)-3,6-dimethyl-2,4(1H, 3H)-pyrimidinedione] (5) are described. Compound 3 was prepared by the reaction of N-methylurethane with diketene, followed by alkali treatment, and 5 was obtained by treatment of 1-(2-hydroxyethyl)-3,6-dimethyl-2,4(1H, 3H)-pyrimidinedione (4) with paraformaldehyde and hydrochloric acid in quantitative yield. Bromination of 5 was carried out with 47% hydrobromic acid to give 5,5'-methylenebis[1-(2-bromoethyl)-3,6-dimethyl-2,4-(1H, 3H)-pyrimidinedione] (6). The reaction of 6 with thiourea afforded 7 and subsequent treatment fo 7 with sodium hydroxide gave 5,5'-methylenebis[1-(2-mercaptoethyl)-3,6-dimethyl-2,4(1H, 3H)-pyrimidinedione] (9). Compound 9 was oxidized to 8,11,15,18-tetramethyl-3,4-dithia[6.1](1.5)-1,2,3,4-tetrahydro-2,4-dioxopyrimidinophane (10) with iodine under conditions of high dilution.

• 公益社団法人日本薬学会の論文
• 1986-04-25

著者

• 木下 敏夫

  Faculty of Pharmaceutical Sciences, Nagasaki University

• 古川 淳

  Faculty of Pharmaceutical Sciences, Nagasaki University

• 木下 敏夫

  School of Pharmaceutical Sciences, Nagasaki University

• 木下 敏夫

  School Of Pharmaceutical Sciences Nagasaki University

• 田中 宏和

  Faculty of Pharmaceutical Sciences, Nagasaki University

• 田中 宏和

  Faculty Of Pharmaceutical Sciences Nagasaki University

関連論文

• Stable Sulfur Ylides. XII. : Reaction of 3-Alkyl(aryl)thio-silyloxydienes Derived from Stable Sulfur Ylides with Aromatic Aldehydes. : Synthesis and Structure of Thiolanium Ylides
• An Efficient Synthesis of Phthalides by Diels-Alder Reaction of Sulfur-Substituted Furanones with Silyloxydienes : A Formal Synthesis of Mycophenolic Acid
• An Efficient Synthesis of 2(5H)-Furanone and Furan Derivatives Using 3-(Phenylthio)propenal as a 1,3-Dipolar Synthon
• Pyrimidine Derivatives. X. Synthesis of New Tricyclic Hetero Compounds Possessing a Pyrimidine Ring : 8,1,3,10-Thiatriazatricyclo[4.3.0.0^]-dodecanes and 8,1,3,10-Thiatriazatricyclo[4.4.0.0^]tridecanes
• Studies on the Heterocyclic Compounds. XIX. A Novel Ring Isomerization of 3-Ylideneaminoimidazo [4,5-c] pyridazines
• Studies on the Pyridazine Derivatives. XVII. Structural Studies on the Product of 3-Hydrazino-4-aminopyridazine with Formic Acid (A Novel Ring Isomerization)
• Studies on the Pyridazine Derivatives. XVI. Reaction of 3-Alkoxy-4-nitro-(and 4,6-dinitro) pyridazine 1-Oxides with Amines
• Studies on the Pyridazine Derivatives. XIV. Synthesis and Reaction of Pyrimido [4,5-c] pyridazines
• Studies on the Synthesis of Pyridazine Derivatives. XIII. Synthesis of Imidazo-[4,5-d]- and v-Triazolo[4,5-d]pyridazine Derivatives and Reaction of 4-Alkoxy-v-triazolo[4,5-d]pyridazines with Various Amines
• Studies on the Synthesis of Pyridazine Derivatives. XII. Synthesis of 4,5-Diaminopyridazine Derivatives
• Studies on the Synthesis of Pyridazine Derivatives. X. Reaction of 3,6-Dimethoxy-4-nitropyridazine 1-Oxide with Alkyl Halides
• Studies on the Synthesis of Pyridazine Derivatives. IX. Synthesis of 10H-Pyridazino (3,2-b) quinazolin-10-one and Its Derivatives. (3)
• Pyrimidine Derivatives. VIII. One-Step Synthesis of 3,4-Dyhydro-pyrimido[6,1-c][1,4]oxazine Derivatives by Reactions of 5-Bromo-1-(2-bromoethyl)-6-bromomethyl-2,4-(1H, 3H)-pyrimidinedione with Sodium Alkoxides and 2-Nitropropane
• A Short and Convergent Synthesis of the Phytoalexins Vignafuran, 6-Demethylvigafuran, and Moracin M via Directed Lithiation Reaction
• A Facile Synthesis of Benzo[b]furan Derivatives Including Naturally Occurring Neolignans via Regioselective Lithiation of ortho-Cresols Using the Bis(dimethylamino)phosphoryl Group as a Directing Group
• The Directed ortho-Lithiation of Aryl Tetramethylphosphorodiamidates
• Correlations between Carbon-13 Nuclear Magnetic Resonance Chemical Shifts and Reactivities of Siloxybutadienes and Siloxyazabutadienes in the Diels-Alder Reaction with Dimethyl Acetylenedicarboxylate
• Reactions of Lithiated ortho-Toluamides and Related Compounds with Vinylsilanes : Syntheses of 1-Tetralones and 1-Naphthols
• Stable Sulfur Ylides. X. : Reactions of Carbonyl-Stabilized Sulfonium Ylides with Acetyl Chloride
• Stable Sulfur Ylides. XI. : Facile Preparation of Silyloxydienes from Stable Sulfur Ylides
• LITHIATION OF ORTHO-TOLYL TETRAMETHYLPHOSPHORODIAMIDATES : A FACILE SYNTHESIS OF 2-ARYLBENZOFURANS INCLUDING NEOLIGNAN, CARINATIN
• ORTHO-LITHIATION OF PHENOLS USING THE BIS(DIMETHYLAMINO)PHOSPHORYL GROUP AS A DIRECTING GROUP
• Ring Clreavage Reaction of 1,3-Oxazine-2,4(3H)-dione Derivatives with Amines
• Total Synthesis of the Antibiotic WS-5995A Using a Key Reaction of o-Toluamide Anions with Homophthalic Anhydrides
• Regioselective Syntheses of Substituted Thioxanthen- and Selenoxanthen-9-one Derivatives
• Primidine Derivatives. V. : Synthesis and Nucleophilic Reactions of 5-Bromo-6-bromomethyl-1-(2-bromoethyl and 2-bromopropyl)-3-methyl-2,4(1H, 3H)-pyrimidinedione
• Synthesis and Reactions of 2,3-Dihydrothiazolo[3,2-α]pyrimidine Derivatives(Organic,Chemical)
• Synthesis of 5,5'-Mehylenebispyrimidine Derivatives and 3,4-Dithia[6.1](1.5)pyrimidinophane
• 安定イオウイリドの研究(第9報)Dimethylsulfonium AcetylcarbamoylmethylideとIsoquinoline 2-Oxideとの反応
• Stable Sulfur Ylides. VIII. The Reactions of 1,3-Oxazin-4-one Derivatives
• Stable Sulfur Ylides. VII. The Reaction of Dimethylsulfonium Acetylcarbamoylmethylide with Quinoline 1-Oxide
• Triphenylphosphonium Allylide類と塩基との反応
• 安定イオウイリドの研究(第6報)Dimethylsulfonium AcetylmethoxycarbonylmethylideおよびDimethylsulfonium DiacetylmethylideとIsoquinoline 2-Oxideとの反応
• Stable Sulfur Ylides. V. Syntheses of α-Acylfuran Derivatives by Thermal and Photochemical Reaction of Allylides
• Stable Sulfur Ylides. IV. Reaction of Dimethylsulfonium Acetylmethoxycarbonylmethylide and Dimethylsulfonium Diacetylmethylide with Quinoline 1-Oxide
• Stable Sulfur Ylides. III. Reaction of Stable Sulfonium Allylides and Oxosulfonium Allylides with Alkoxides
• Stable Sulfur Ylides. II. : Syntheses of Stable Sulfonium Allylides and Oxosulfonium Allylides
• Pyrimidine Derivatives. XI. Facile Carbon-Carbon Bond-Cleavage Reaction of 6-Bromomethylpyrimidinediones and (2,4-Dioxo-1,2,3,4-tetrahydropyrimidin-6-yl)methyl Nitrate via 6-Formyl Derivatives
• Reaction of Lithiated Senecioamide and Related Compounds with Benzynes : Efficient Syntheses of Naphthols and Naphthoquinones
• ACRIDONES FROM THE REACTION OF N-LITHIO ANTHRANILATES WITH BENZYNES. A SHORT SYNTHESIS OF ACRONYCINE

もっと見る 閉じる

スポンサーリンク