Studies on 1,4-Benzothiazines. II. Acetylation of 2,3-Dihydro-3-imino-4H-1,4-benzothiazine

スポンサーリンク

概要

• 論文の詳細を見る

• In a previous paper, we described the formation of the 8,5-diazaphenothiazino [8,7-h]-phenothiazine derivative (2) by acetylation of 2,3-dihydro-3-imino-4-methyl-4H-1,4-benzothiazine (1a). This paper deals with the acetylation of the desmethyl derivative (1b). When a suspension of 1b in acetic anhydride was heated under reflux for 2 hr, the bis [1,4] benzothiazino [3,2-b ; 2', 3'-e] pyridine derivative (5a) was obtained instead of the expected analog of 2. The structure of 5a was assigned on the basis of infrared, nuclear magnetic resonance and mass spectral data, and microanalysis. Treatment of 5a with Raney Ni afforded the desulfurized compound 6,which was identical with an authentic sample prepared by acetylation of 2,6-dianilino-4-picoline (7). Deacetylation of 5a was attempted, and the monoacetyl compound 5b and the deacetyl compound 5c were obtained.

• 社団法人日本薬学会の論文
• 1979-10-25

著者

• 栗原 拓史

  Osaka University of Pharmaceutical Sciences

• 平野 弘

  Osaka College of Pharmacy

• 杉山 和明

  Osaka College of Pharmacy

• 永田 修一

  Osaka College of Pharmacy

• 栗原 拓史

  Osaka College Of Pharmacy

関連論文

• Synthetic Studies of (±)-Lysergic Acid and Related Compounds(Organic,Chemical)
• Studies on Indenopyridine Derivatives and Related Compounds. VI. : Synthesis adn Stereochemistry of Ethyl 9.9-Dimethyl-1,2,3,9a-tetrahydro-9H-indeno[2,1-b]pyridine-3-carboxylate as a Possible Intermediate for the Total Synthesis of Lysergic Acid
• A NEW SYNTHESIS OF (±)-LYSERGIC ACID
• Improved Synthesis of 5'-Deoxy-5'-adenosineacetic Acid
• Thermal Elimination of Carbonyl Sulfide from O-Aryl Thionocarbonates of Pyrrolidine-, Piperidine-, and Tetrahydrothiophene-2-ethanol
• Novel Transformation of Azabicyclothionocarbonate to Azaspirolactone
• Molecular Conformations of Aminophenylimidazoles Exhibiting Antiulcer Activities
• NEW ASPECTS OF THE 1,3-DIPOLAR CYCLOADDITION OF THIAZOLIUM N-IMINES WITH DIMETHYL ACETYLENEDICARBOXYLATE (DMAD)
• Studies on Ergot Alkaloids and Related Compounds. XIV. Syntheses of N-Alkyl-4-methyl-2,3,4,4a, 5,6-hexahydrobenzo [f] quinoline-2-carboxamides and Stereochemistry of Diethyl 4-Methyl-1-oxo-1,2,3,4,4a, 5,6,10b-octahydrobenzo [f] quinoline-2,2-dicarboxylate
• Studies on Ergot Alkaloids and Related Compounds. XIII. syntheses and Stereochemistries of 4-Methyl-1,2,3,-4,4a, 5,6,10b-octahydrobenzo[f]quinoline-2-carboxylic Acids
• Studies on 1,4-Benzothiazines. IV. Reactions of 2-Acyl-4H-1,4-benzothiazines with Hydroxylamine, Hydrazine, Guanidine and Acetamidine
• 1,3-DIPOLAR CYCLOADDITION OF THIAZOLIUM N-PHENYLIMIDES WITH ACRYLONITRILE
• 2. チアミン-O-インドール-3-ブロピオネートにおけるピリミジン核とインドール核のスタッキング : 第268回会議研究発表要旨 : ビタミンB研究委員会
• 1,4-Benzothiazineに関する研究(第3報)2-Acyl-4-methylbenzothiazine類およびその関連化合物の反応性
• ビタミンB_1とブロムシアンの反応におけるO-カルバモイルチオクロームの生成について
• 2.チアミンとブロムシアンとの反応生成物(ビタミンB研究委員会 : 第260回会議研究発表要旨)
• Studies on 1,4-Benzothiazines. II. Acetylation of 2,3-Dihydro-3-imino-4H-1,4-benzothiazine
• リポ酸の生合成におけるn-オクタン酸への硫黄の導入
• Studies on 1,4-Benzothiazines. I. Synthesis of 2,3-Dihydro-3-imino-4H-1,4-benzothiazines and Acetylation of the N-Methyl Derivative
• Isoalloxazine関連化合物の新しい合成法
• d-ビオチンの立体特異的全合成
• イソビオプテリンの副生を伴わぬビオプテリンの合成
• チアミンとその関連化合物の新しい分解と合成反応に関する研究
• Meisenheimer Rearrangement of Azetopyridoindoles. VII. Ring Expansion of 2-Phenylhexahydroazeto[1', 2' : 1,2]pyrido[3,4-b]indoles by Oxidation with m-Chloroperbenzoic Acid
• [3,3]Sigmatropic Ring Expansion of Cyclic Thionocarbonates. VII. On the Formation of 8-Membered Thionocarbonates as the Intermediates
• [3,3]Sigmatropic Ring Expansion of Cyclic Thionocarbonates. VI. Regioselective Wohl-Ziegler Bromination of 10-Membered Thiolcarbonates
• Chemistry of Tetrahydro-1,3-oxazin-2-one : New Method for the Synthesis of Indoloquinolizidine Derivatives
• MEISENHEIMER REARRANGEMENT OF 2-ETHENYL-1,4,5,10b-TETRAHYDRO-2H-AZETOPYRIDO[3,4-b__-]INDOLE N-OXIDES : NEW ROUTE TO THE 12(S)CARBA-EUDISTOMIN SKELETON
• Reductive Cyclization of o-Nitrobenzylideneacetylacetone Analogues
• Studies on Indenopyridine Derivatives and Related Compounds. III. Stereochemistry of 1-Substituted 4,9-Dihydroxy-9-phenyl-1,2,3,4,4a, 9a-hexahydro-9H-indeno [2,1-b] pyridines
• Reaction of Pyrazolo [1,5-α] pyrimidine Derivatives with Nucleophiles. V. X-Ray Determination of the Molecular Structure of a Reaction Product of 6,7-Diethoxycarbonylpyrazolo [1,5-α] pyrimidine-3-carbonitrile with N-Methylindole
• A New Method for the Preparation of 2-Hydroxymethyl-3-quinolinecarboxylic Acid Lactone Derivatives
• Reactions of Pyrazolo [1,5-α] pyrimidine Derivatives with Nucleophiles. IV. Some Reactions of 1,4-Dihydrocyclopent [b] indoles
• THE REACTION OF 1,4-DIHYDROCYCLOPENT [b] INDOLES WITH DIMETHYL ACETYLENEDICARBOXYLATE
• Reaction of 3-[3-(2-Nitrophenyl)-2-propenylidene]-2,4-pentanedione with Hydroxylamine Hydrochloride. Formation of a 2-Chloromethyleneindolin-3-one
• Reactions of Pyrazolo [1,5-a] pyrimidine Derivatives with Nucleophiles. III. Nucleophilic Addition to 6,7-Bis (ethoxycarbonyl) pyrazolo [1,5-a] pyrimidine-3-carbonitrile in the Presence of Triethyloxonium Fluoroborate
• Synthesis and Reactions of Ethyl 6-Acetyl-2,3-diphenylimidazo [1,2-a] pyrimidine-5-carboxylate and Related Compounds
• SYNTHESIS AND X-RAY CRYSTAL STRUCTURE DETERMINATION OF 1,4-DIHYDROCYCLOPENT [b] INDOLES
• Ring Transformations of 6H-Cyclopropa [e] pyrazolo [1,5-a] pyrimidine. III. Synthesis and X-Ray Crystal Structure Determination of a 1-Pyrazol-3-ylpyrrole-2-carboxylic Acid
• Reactions of Pyrazolo [1,5-α] pyrimidine Derivatives with Nucleophiles. I. Nucleophilic Addition to 6,7-Dicarbethoxypyrazolo [1,5-α]-pyrimidine-3-carbonitrile in the Presence of Boron Trifluoride Etherate
• Ring Transformations of 6H-Cyclopropa[5a, 6a]pyrazolo[1,5-a]pyrimidine. II. Reaction of 5a-Acetyl-6a-carbethoxy-5a, 6a-dihydro-6H-cyclopropa[5a, 6a]pyrazolo[1,5-a]pyrimidine-3-carbonitriles with N-Methylaniline
• Reactions of Ethyl 3-Ethoxymethylene-2,4-dioxovalerate and Ethyl Ethoxymethyleneoxaloacetate with Indole Analogs
• Studies on Ergot Alkaloids and Related Compounds. XII. Syntheses of Ethyl 4-Methyl-2,3,4,4α, 5,6-hexahydrobenzo[f]quinoline-2-carboxylate and its Dihydro Derivative
• Formation of 2-Acetyl-3-hydroxy-5-phenylmaleimide from Ethyl 3-Ethoxy-methylene-2,4-dioxovalerate and Phenylhydroxylamine
• Studies on Ergot Alkaloids and Related Compounds. XVI. On the So-called Bohlmann Absorption of 2,4-Disubstituted Octahydrobenzo [f] quinoline Derivatives
• Studies on Ergot Alkaloids and Related Compounds. XV. Reductions of cis- and trans-4-Methyl-2-methylen-3-oxo-1,2,3,4,4a, 5,6,10b-octahydrobenzo [f] quinolines and Preparation of trans-syn-2,4-Dimethyl-1,2,3,4,4a, 5,6,10b-octahydrobenzo-[f] quinoline
• REACTION OF METHYL VINYL KETONE CYANOHYDRIN PHOSPHATE WITH AROMATIC COMPOUNDS
• Meisenheimer Rearrangement of Azetopyridoindoles. V. Synthesis of 9-Methyl-12-carbaeudistomin and Related Compounds
• 1,4-and 1,7-Addition Reactions of 4-(Substituted benzylidene)-3,5-dimethylisopyrazoles
• Reaction of 4-(o-Nitrobenzylidene)-3,5-dimethylisopyrazole with Acyl Chlorides
• Studies on Indenopyridine Derivatives and Related Compounds. I. Syntheses and Stereochemistries of 1-Substituted 1,2,3,4,4a, 9a-Hexahydro-4-hydroxy-9H-indeno [2,1-b] pyridines and Related Compounds
• Preparation of Thiamine from Dihydrothiamine
• A NEW SYNTHESIS OF BIARYLS
• Meisenheimer Rearrangement of Azetopyridoindoles. III. Synthesis of 3,6-Epoxyhexahydroazocino[5,4-b]indoles
• Meisenheimer Rearrangement of Azetopyridoindoles. VI. Synthesis of 12-Carbaeudistomin and Related Compounds
• Application of Cyanophosphates in Organic Synthesis. Reactivity of α-Cyano-α-diethylphosphonooxy Anions(Organic,Chemical)
• Allylic Rearrangement of Cyanophosphates. III. : Reaction of Acyclic Enone Cyanophosphates
• Studies on Isopyrazole Derivatives and Related Compounds. I. Structure of Condensation Product of Nitrobenzylideneacetylacetone with Hydrazine Dihydrochloride
• [3,3]Sigmatropic Ring Expansion of Cyclic Thionocarbonates. IV. Relatioship between Ring Size of Cyclic Thionocarbonates and Geometry of Created Double Bond in Medium- and Large-Membered Thiolcarbonates
• Reductive Deoxygenation of α, β-Unsaturated Ketones via Cyanophosphates by Lithium in Liquid Ammonia
• Synthesis and Cycloaddition Reaction of 2-Cyano-3-indoleacetonitriles
• CYANOPHOSPHORYLATION OF KETONES AND ALDEHYDES USING DIETHYL PHOSPHOROCYANIDATE (DEPC)
• New Route to 1-(5-Imidazolyl)ribofuranoid Glycals from Ribofuranosyl Chloride and 5-Lithio-imidazole
• RECYCLISATION OF 2-OXOTETRAHYDRO-1,3-OXAZINES ACCOMPANIED BY DECARBOXYLATION : A CONVENIENT SYNTHESIS OF TETRAHYDROPYRIDINE, QUINOLIZIDINE, AND INDOLIZIDINE SKELETONS
• A New Synthesis of Allenic Nitriles from Ynones via Cyano Phosphates
• NEW ROUTE TO (Z)-ALLYLIC SULFIDES VIA A 10-MEMBERED THIOLCARBONATE
• Allylic Rearrangement of Cyanophosphate. II. Synthesis of β-Cyano-α, β-unsaturated Ketones
• ALLYLIC REARRANGEMENT OF α, β-UNSATURATED KETONE-DIETHYL PHOSPHOROCYANIDATE ADDUCTS

もっと見る 閉じる

スポンサーリンク