Acid-catalyzed Cyclization of Chalcones derived from Various Nitrogenous Heteroaromatic Compounds. II

スポンサーリンク

概要

• 論文の詳細を見る

• 1-Cinnamoylisoquinoline (I) was treated with perchloric acid in ethanol to give 2,5-dihydro-1-oxo-3-phenyl-[1H] pyrrolo [2,1-α] isoquinolinium perchlorate (V) in the yield of 48.1%. V was derived to 1-(4-nitrobenzoyloxy)-3-phenyl-[1H] pyrrolo [2,1-α] isoquinoline (VI) by means of the Shotten-Baumann reaction. 3-Methylquinoxalin-2-yl 4-phenyl-1,3-butadienyl ketone (VIIa) was treated with acid to give 3-hydroxy-4-methyl-1-styrylpyrrolo [1,2-α] quinoxalinium perchlorate (VIIIa) in quantitative yield. VIIIa was treated with diazomethane to give 3-methoxy-4,5-dimethyl-1-styrylpyrrolo [1,2-α] quinoxalinium perchlorate (XI). VIIIa gave a monobromide (XIIa) on treatment with bromine in carbon tetrachloride. The rate of acid-catalyzed cyclization of 3-methylquinoxalin-2-yl 4-(4-nitrophenyl)-1,3-butadienyl ketone (VIIb) was slower than that of VIIa. Attempts to cyclize XIV intramolecularly to 2,5-dihydro-1-phenylpyrrolizin-3 [1H]-one (XVI) were unsuccessful under various conditions.

• 公益社団法人日本薬学会の論文
• 1983-02-25

著者

• 山崎 高應

  Faculty of Pharmaceutical Sciences, University of Toyama

• 山崎 高広

  富山医科薬科大学

• 山崎 高應

  Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

• 的場 勝英

  Faculty Of Pharmaceutical Sciences Toyama Medical & Pharmaceutical University

• 的場 勝英

  Faculty Of Pharmaceutical Sciences Osaka University

• 宮田 侑生子

  Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University

• 宮田 侑生子

  Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

関連論文

• Synthetic Studies of Azaflavonoids. I. Studies on the Synthesis of 5-Azaflavone
• 8,13-Diazagona-1,3,5 (10)-triene-12-ones, Synthesis and Stereochemistry
• A Stereocontrolled Synthesis of (±)-Emetine and (±)-Protoemetinol by Intramolecular Michael Reaction
• Chemistry of 2-Methoxy-2,5-cyclohexadienone. V. Photochemical Rearrangement and Oxidation of 2-Methoxy-4-methyl-4-phenyl-2-cyclohexenone and 2-Methoxy-4-methyl-4-phenyl-2,5-eyclohexadienone(Organic,Chemical)
• 薬理活性志向のヘテロ環の合成研究
• Synthesis in the Diazasteroid Group. XX. Synthesis of the 5,14-Diazasteroid System(Organic,Chemical)
• チオアミド官能基の特性を利用する複素環合成
• An Efficient Total Synthesis of (±)-Epilupinine and (±)-Lupinine from a Common Quinolizidine Intermediate
• Favorskii Reaction of 2-Bromobicyclo[3.3.1]nonan-3-one
• Reaction of Aliphatic Dicarboxylic Acids with Acyl Chlorides in the Presence of Aluminum Chloride
• Ketene-S, N-acetals as Synthetic Intermediates for Heterocycles. Reaction of Ketene-S, N-acetals with Aryl Isocyanates
• Chemistry of 2-Methoxy-2,5-cyclohexadienone. IV. Photochemistry of 2-Methoxy-4,4-diphenyl-2,5-cyclohexadienone and 4-Dichloromethyl-2-methoxy-4-methyl-2,5-cyclohexadienone
• Reduction of Vinylogous Thioesters with Lithium Aluminum Hydride. II. Reduction of 2-Methyl-3-phenylthio-5-substituted-2-cyclopentenones
• Reduction of Vinylogous Thioesters with Lithium Aluminum Hydride. I. Reduction of β-Phenylthio-α, β-unsaturated Cyclic Ketones
• Chemistry of 2-Methoxy-2,5-cyclohexadienones. III. Syntheses of 2-Methoxy-4,4-diphenyl-2,5-cyclohexadienone and 4-Dichloromethyl-2-methoxy-4-methyl-2,5-cyclohexadienone
• Structural Modification of Bioactive Compounds. II. Syntheses of Aminophosphonoic Acids
• Chemistry of 2-Methoxy-2,5-cyclohexadienones. II. Oxidation of 2-Methoxy-4,4-dimethyl-2,5-cyclohexadienone
• Synthesis in the Diazasteroid Group. XXI. An Alternative Synthesis of the 8,16-Diazasteroid System
• KETENE-S, N-ACETALS AS SYNTHETIC INTERMEDIATES FOR HETEROCYCLES. A NOVEL SYNTHESIS OF POLYFUNCTIONALIZED PYRIDINE-2-THIONES
• Structural Modification of Bioactive Compounds. I. Syntheses of Vitamin D Analogues I
• Nitration of 2-Cyclohexenone Derivatives and Some Reactions of the Products
• AN EASY SYNTHESIS OF MONOMETHYL MALONATE DERIVATIVES
• Activated Lactams. VI. The Cycloaddition Reaction of Cyclic Ketene-S, N-acetals with Dimethyl Acetylenedicarboxylate
• Studies on the Alkaloids of Menispermaceous Plants. CCLIX. Alkaloids of Menispermum dauricum DC. (Suppl. 7). Structures of Acutumine and Acutumidine, Chlorine-Containing Alkaloids with a Novel Skeleton
• The Chemistry of Lactim Ethers. II. Reaction of Lactim Ethers with 2-Carbethoxymethyl Piperidines
• 水素化リチウムアルミニウムによるVinylogous Esterの還元(第2報)
• 水素化リチウムアルミニウムによるVinylogous Esterの還元(第1報)
• オオツヅラフジSinomenium acutum REHD.et WILS.微量成分の検索
• 1,4,7-Dioxaselenocines from 1,3-Oxaselenoles(Organic,Chemical)
• Acid-catalyzed Cyclization of Chalcones derived from Various Nitrogenous Heteroaromatic Compounds. II
• SYNTHESES OF VITAMIN D ANALOGUES 1
• Chemistry of 2-Methoxy-2,5-cyclohexadienones. I. Photochemistry of 2-Methoxy-4,4-dimethyl-2,5-cyclohexadienone
• A FACILE SYNTHESIS OF 2-METHOXY-4,4-DIMETHYL-2,5-CYCLOHEXADIENONE VIA 5,5-DIMETHYL-2-NITRO-1,3-CYCLOHEXADIENOL
• Michael Addition of [1H] Pyrrole
• Synthesis in the Diazasteroid Group. XIX. Synthesis of the 9,13-Diazasteroid System
• The Chemistry of Lactim Ethers. V. Reaction of Lactim Thioethers with β-Aminoesters
• Acid-catalyzed Cyclization of Chalcones derived from Various Nitrogenous Heteroaromatic Compounds
• A Convenient Synthesis of Monocyclic β-Lactams by Means of Solid-Liquid Phase Transfer Reactions
• Synthesis in the Diazasteroid Group. XV. Syntheses of the 5,9- and 8,13-Diazasteroids
• Synthesis in the Diazasteroid Group. XIV. Synthesis of the 13,15-Diazasteroid System
• Reaction of Lactim Thioethers with 1-Carbethoxymethyl-1,2,3,4-tetrahydroisoquinoline
• Synthesis of 8,10-Diaza-estrane
• Synthetic Studies of Azaflavonoids. II. Synthesis of 6-Azaflavonoids
• Studies on O-Alkylated Imides. II. Some Reactions of O-Ethyl Succinimide and O-Ethyl 4,4-Dimethyl-glutarimide
• Reduction of O-Alkylated Imides
• Synthesis of Zwitterionic Pyridazine Derivatives. I
• Synthesis in the Diazasteroid Group. XVIII. Syntheses of the 9,17-Diazasteroid System
• Synthesis in the Diazasteroid Group. XVII. Syntheses of the 4,11-Diazasteroid System
• Reaction of Vinylogous Esters with Grignard Reagent
• Synthesis in the Diazasteroid Group. IV. A Synthesis of 2,3-Dimethoxy-8,14-diaza-15-oxo-gona-1,3,5 (10)-triene
• 水素化リチゥムアルミニゥムによるVinylogous Esterの還元(第7報) : α-Alkoxyl基置換6員環Vinylogous Esterに関して
• 水素化リチウムアルミニウムによるVinylogous Esterの還元(第6報)
• 水素化リチウムアルミニウムによるVinylogous Esterの還元(第5報)
• 水素化リチウムアルミニウムによるVinylogous Esterの還元(第4報)
• Vinylogous Esterの接触還元(第1報)
• 水素化リチウムアルミニウムによるVinylogous Esterの還元(第3報)
• チオアミド官能基の特性を利用する複素環合成

もっと見る 閉じる

スポンサーリンク