Studies on Tertiary Amine Oxides. XLVII. Reaction of Quinoline 1-Oxide Derivatives with Cyanogen Bromide
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概要
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Reactions of various substituted quinoline 1-oxides with cyanogen bromide in ethanol were investigated. The corresponding ethyl N-(8-quinolyl) carbamates were formed in most cases, but their yields were rather low except reactions of N-oxides of 4-quinolinol (If), 4-aminoquinoline (Ig), 2-quinolinol (IXf), 5-nitroquinoline (XXVI) and 6-chloroquinoline (XXX). In addition to 8-quinolylcarbamates, 2-quinolylcarbamates (VIc and VIe) were obtained from reactions of 4-ethoxyquinoline 1-oxide (Ic) and lepidine 1-oxide (Ie), and further the 6-quinolylcarbamate (VII) was also isolated in the latter case. The reaction of 4-quinolinol 1-oxide (If) gave the 3-quinolylcarbamate (VIII) as the main product besides 8-quinolyl derivatives, IIf and IIi. 2-Imino-1,2,4-oxadiazolo [2,3-α] quinoline hydrobromide (XVI) was produced without the participation of ethanol in a good yield of 65% from the reaction of 2-aminoquinoline 1-oxide (IXg). From 8-ethoxycarbonylaminoquinoline 1-oxide (XX), a small amount of 2,8-bis (ethoxycarbonylamino)-quinoline (XXI) was obtained. The features and mechanisms of some reactions were also discussed.
- 公益社団法人日本薬学会の論文
- 1974-07-25
著者
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浜名 政和
Faculty of Pharmaceutical Sciences, Kyushu University
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浜名 政和
Faculty Of Pharmaceutical Sciences Kyushu University
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熊懐 節子
Faculty of Pharmaceutical Sciences, Kyushu University
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熊懐 節子
Faculty Of Pharmaceutical Sciences Kyushu University
関連論文
- 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
- Synthese von Derivaten der Cinchona-Alkaloide. XXXIII. Synthese von 2'-Cyanoderivaten der Alkaloide der Chinin-Reihe
- 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
- 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
- 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)
- 1,1-Disubstituted 1,2,3,4-Tetrahydroisoquinoline Derivatives from Isoquinolines
- Studies on Tertiary Amine Oxides. LXXIII. Substitution of Aromatic N-Oxides with Radicals produced from Azo Compounds
- 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. 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
- 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
- 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)
- 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.
- Studies on Tertiary Amine Oxides. XLIX. Reactions of Pyridine and Quinoline N-Oxides with 1 (10)-Dehydroquinolizidine