Studies on Tertiary Amine Oxides. LXIX. Reactions of 2-Chloromethylquinoline Derivatives with 2-Nitropropane

スポンサーリンク

概要

• 論文の詳細を見る

• Reactions of 2-chloromethylquinoline (1), its N-oxide (2) and their nitro derivatives with the sodium salt of 2-nitopropane were investigated. O-Alkylation occurred with 1 and 2,giving 2-quinolinecarboxyaldehyde (5 : 11%) and its N-oxide (6 : 10%). The reaction of 2-chloromethyl-5-nitroquinoline (3b) gave both the O-alkylation product, 5-nitro-2-quinolinecarboxyaldehyde (7 : 21%), and the C-alkylation products, 2-(2-methyl-2-nitropropyl)-5-nitroquinoline (8b : 24%) and 2-(2-methyl-1-propenyl)-5-nitroquinoline (9b : trace). In the reactions of the 6-nitro (3c) and 8-nitro (3d) derivatives of 1,the 2-(2-methyl-2-nitropropyl) quinolines (8c : 86% and 8d : 63%) were predominantly formed. In contrast, the reactions of the 4-nitro (4a), 5-nitro (4b) and 6-nitro (4c) derivatives of 2 produced the corresponding 2-(2-methyl-1-propenyl) quinoline N-oxides (11a : 53%, 11b : 20% and 11c : 66%) as main products, accompanied by small amounts of the 2-(2-methyl-2-nitropropyl) compounds (10a : 20% and 10b : 17%).

• 1980-08-25

著者

• 佐伯 清太郎

  Faculty of Pharmaceutical Sciences, Kyushu University

• 野田 浩司

  産業医科大学薬剤部

• 浜名 政和

  Faculty of Pharmaceutical Sciences, Kyushu University

• 西川 理

  Faculty of Pharmaceutical Sciences, Nagasaki University

• 西川 理

  九州大学薬学部薬化学教室

• 西川 理

  Faculty Of Pharmaceutical Sciences Nagasaki University

• 野田 浩司

  Faculty of Pharmaceutical Sciences, Kyushu University

• 佐伯 清太郎

  Faculty Of Pharmaceutical Sciences Kyushu University

• 浜名 政和

  Faculty Of Pharmaceutical Sciences Kyushu University

関連論文

• Practical Synthesis of Optically Active 6,6,Dichloro-2,2'-dipfenic Acid and Its Dimethyl Ester
• Metabolic Studies on Polychlorinated Biphenyls. II. Metabolic Fate of 2,4,3', 4'-Tetrachlorobiphenyl in Rats
• Studies on Tertiary Amine Oxides. LVII. Re-examination of the Reaction of Quinoline 1-Oxide with Acetic Anhydride, and the Related Reactions
• Studies on Tertiary Amine Oxides LXXXII. : The Reaction of 1-Oxido-4(or 2)-pyridinediazonium Tetrafluoroborate with Olefins in the Presence of Palladium Complex
• Studies on Tertiary Amine Oxides. LXXVII. The Pseudo-Gomberg Reaction of 4-and 2-Aminopyridine 1-Oxides
• Reduction of 1-Methyl-3-and-4-methoxycarbonyl Pyridinium Iodide with Sodium Borohydride
• Studies on Tertiary Amine Oxides. XLIII. Reactions of Aromatic N-Oxides with Alkoxyindoles in the Presence of Acylating Agents
• Studies on Tertiary Amine Oxides. XL. Reactions of Aromatic N-Oxides with Oxindoles in the Presence of Acylating Agents
• Studies on Tertiary Amine Oxides. XXXIX. Reactions of Aromatic N-Oxides with Indoles in the Presence of Acylating Agents
• Reaction of Aromatic N-Oxides with Indoles in the Presence of an Acylating Agent
• Studies on the Heterocyclic Compounds. XXI. A New Alkylation of Pyridazines with Nitromethane and Nitroethane
• Synthese von Derivaten der Cinchona-Alkaloide. XXXIII. Synthese von 2'-Cyanoderivaten der Alkaloide der Chinin-Reihe
• Inductive Effect of Polychlorinated Biphenyls Mixture and Individual Isomers on the Hepatic Microsomal Enzymes
• 2-Chloroおよび1,4,8-Trichlorodibenzofuranの合成とそのマウス成長ならびにラット肝ミクロゾ-ム薬物代謝酵素系に及ぼす影響 (油症とPCBに関する研究)
• 過硫酸アンモニウム存在下におけるQuinolinium Perchlorate類のα-オキシアルキル化反応
• Studies on Tertiary Amine Oxides. LXIX. Reactions of 2-Chloromethylquinoline Derivatives with 2-Nitropropane
• Studies on Tertiary Amine Oxides. LXII. A Novel Formation of Quinolinium Methylides by the Reaction of Quinoline 1-Oxides with Active Methylene Compounds in the Presence of an Acylating Agent
• A New Conversion Method from (-)-Limonene to Nepetalactones
• Conversion of (-)-Limonen-10-ol to 11-Deoxyprostaglandin
• Formal Synthesis of Brefeldin A from (+)-Limonen-10-ol
• Studies on Tertiary Amine Oxides. XIV. Reactions of N-(p-Dimethylaminophenyl) nitrones having Pyridine, Quinoline or its N-Oxide, as α-Substituent with Carbon Disulfide.
• Studies on Tertiary Amine Oxides. XIII. Reactions of N-(p-Dimethylaminophenyl) nitrones having Pyridine N-Oxide, Quinoline or its N-Oxide as α-Substituent.
• Studies on Tertiary Amine Oxides. XLIV. Reactions of Aromatic N-Oxides with N-Acylmethylpyridinium Salts in the Presence of Acylating Agents
• Studies on Azole Compounds. III. Reactions of Oxazole N-Oxides with Phosphoryl Chloride and Acetic Anhydride
• Reduction of N-(α-Acyl-2-quinolylmethyl) pyridinium Perchlorate
• Studies on Tertiary Amine Oxides. LXI. Some Reactions of 2-Phenylquinoline 1-Oxide and Its Derivatives
• 2-(2-Quinolyl)-または2-(2-Pyridyl)cyclohexanoneと有機過酸との反応
• Beckmann転位条件下における2-(2-Quinolyl)-または2-(2-Pyridyl)-cyclohexanone Oximeの新しい閉環反応
• Studies on Tertiary Amine Oxides. LXXXI. Formation of 1-lsoquinoliniomethylides by the reaction of Isoquinoline 2-Oxide with Cyanoacetic Acid and Benzoylacetonitrile in the Presence of Acetic Anhydride
• Studies on Tertiary Amine Oxides. LXXX. Reaction of Quinoline 1-Oxide with Phenylacetic Anhydride
• Studies on Tertiary Amine Oxides. XXXVIII. Reaction of Quinoline 1-Oxide with N-Acylmethylpyridinium Salts in the Presence of Acylating Agents
• The Pseudo-Gomberg Reaction of Benzene Derivatives with 1-Substituted Pyrroles
• A New Synthetic Approach to 8-Chloroflavins and Their Conversion into 8-(Substituted-amino) flavins
• Studies on Tertiary Amine Oxides. LIX. A New Total Synthesis of dl-Allomatridine
• Studies on Tertiary Amine Oxides. LVIII. Reactions of Substituted Dehydroquinolizidines with Pyridine N-Oxide. (2)
• Studies on Tertiary Amine Oxides. LXXIII. Substitution of Aromatic N-Oxides with Radicals produced from Azo Compounds
• Studies on Tertiary Amine Oxides. LV. Reactions of N-Alkoxyquinolinium Salts with Enamines of Ketones. (1)
• Studies on Tertiary Amine Oxides. LXVI. Reactions of Quinoline 1-Oxide Derivatives with Tosyl Chloride in the Presence of Triethylamine
• Studies of Tertiary Amine Oxides. LXV. Reaction of Quinoline 1-Oxide with Tosyl Chloride in the Presence of Triethylamine
• Studies on Tertiary Amine Oxides. LXXIX. Reactions of 2-Ethoxycarbonyl-1-hydroxyindole in the Presence of Acylating Agents
• The Reaction of α-Substituted Ketones with N-Alkylhydroxylamines
• Studies on Tertiary Amine Oxides. LXXVI. Reactions of Aromatic N-Oxides with 1,3-Cyclohexanediones in the Presence of Acetic Anhydride
• Studies on Tertiary Amine Oxides. LXXIV. Reactions of Aromatic N-Oxides with 2-Phenyl-2-Thiazolin-4-one in the Presence of Acetic Anhydride
• Studies on Tertiary Amine Oxides. LXXV. Reactions of Aromatic N-oxides with Meldrum's Acid in the Presence of Acetic Anhydride
• Studies on Tertiary Amine Oxides. LXXII. Some Nucleophilic Reactions of 1-Hydroxy-2-phenylindole
• Studies on Tertiary Amine Oxides. LXXI. Some Electrophilic Reactions of 1-Hydroxy-2-phenylindole
• Stereoselective Alkylation of 1-Oxoquinolizidine
• 第3級アミンオキシドに関する研究(第60報) : アシル化剤の存在下における3,2'-Diquinolyl 1-Oxideと求核剤との反応
• Studies on Tertiary Amine Oxides. XXXVII. Reactions of Aromatic N-Oxides with Enol Ethers in the Presence of Benzoyl Chloride
• Photoreaction of N-Ethoxyquinolinium Perchlorate in Methanol
• 第3級アミンオキシドに関する研究(第36報) : アシル化剤の存在下における芳香族アミンオキシドと1-Morpholinoisobuteneとの反応
• Studies on Tertiary Amine Oxides. XXXI. Reactions of Aromatic N-Oxides with Antipyrine in the Presence of Acylating Agents.
• Reactions of Aromatic N-Oxides with Enamines of Cyclohexanone in the Presence of Acylating Agents (3).Reactions of Chloro- and Hydroxy-pyridine and -quinoline N-Oxides
• Studies on Tertiary Amine Oxides. XXVII. Reactions of Aromatic N-Oxides with Enamines of Cyclohexanone in the Presence of Acylation Agents : Reaction of α-and γ-Methyl-pyridine and -quinoline N-Oxides
• Studies on Tertiary Amine Oxides. XXIV. Reactions of Aromatic N-Oxides with Enamines of Cyclohexanone in the Presence of Acylating Agents (1)
• Reactions of Quinoline 1-Oxide with Enamines of Cyclohexanone
• Studies on Tertiary Amine Oxides. LXIV. Reaction of 4-Nitroquinoline 1-Oxide and Related Compounds with Potassium Cyanide
• Studies on Tertiary Amine Oxides. LIV. Reaction of Quinoline N-Oxides with Potassium Cyanate and Tosyl Chloride in Ethanol
• Studies on Tertiary Amine Oxides. XLVII. Reaction of Quinoline 1-Oxide Derivatives with Cyanogen Bromide
• Studies on Tertiary Amine Oxides. XLV. Reaction of Quinoline N-Oxide with Cyanogen Bromide
• Studies on Tertiary Amine Oxides. XXVI. Nitration of 6-Substituted Quinoline 1-Oxides.
• 2,5,2′,5′-Tetrachloro-4-Methylthiobiphenylの合成 (油症とPCBに関する研究報告集-9-)
• Studies on Tertiary Amine Oxides. XLIX. Reactions of Pyridine and Quinoline N-Oxides with 1 (10)-Dehydroquinolizidine

もっと見る 閉じる

スポンサーリンク