Azamorphinan and Related Compounds. I. A Synthesis of 3-Hydroxy-N-methyl-9-azamorphinan (Studies on the Syntheses of Heterocyclic Compounds. CCXIV)
スポンサーリンク
概要
- 論文の詳細を見る
In order to examine the analgesic action of azamorphinan attempt to synthesize 3-hydroxy-N-methyl-9-azamorphinan (III) which has an additional nitrogen in morphinan ring was carried out successfully. Hydrolysis of 2-ethoxycarbonylmethyl-2-(3-methoxyphenyl) cyclohexanone (IX), which was obtained by condensation of 2-(3-methoxyphenyl) cyclohexanone (VIII) with ethyl bromoacetate in the presence of sodium amide, was first examined to give 2-carboxymethyl-2-(3-methoxyphenyl) cyclohexanone (X), whose methylhydrazination with methyl hydrazine afforded 3,4,5,6,7,8-hexahydro-2H, 4aH-4a-(3-methoxyphenyl)-2-methyl-3-oxocinnoline (XI). Secondly, reduction of the preceding compound (XI) with lithium aluminum hydride gave 4a-(3-methoxyphenyl)-2-methyldecahydrocinnoline (XII), which was converted into 3-methoxy-N-methyl-9-azamorphinan (XV) by Pictet-Spengler reaction with formalin and hydrochloric acid. Finally, demethylation of XV with hydrobromic acid afforded 3-hydroxy-9-azamorphinan (III), which was characterized as the picrate of its benzoate (XVI). Furthermore, conformation of XV was discussed.
- 公益社団法人日本薬学会の論文
- 1968-02-25
著者
-
柊木 峯治
グレラン製薬株式会社研究所
-
亀谷 哲治
Pharmaceutical Institute, Tohoku University School of Medicine
-
我妻 永利
グレラン製薬株式会社研究所
-
気賀沢 和雄
Research Laboratories, Grelan Pharmaceutical Co., Ltd.
-
亀谷 哲治
Pharmaceutical Institute Medical Faculty University Of Osaka
-
柊木 峯治
Research Laboratories, Grelan Pharmaceutical Company, Ltd.
-
我妻 永利
Research Laboratories, Grelan Pharmaceutical Co., Ltd.
関連論文
- 医薬品の生物薬剤学的研究(第7報)o-EthoxybenzamideとN-(β-Hydroxybutyryl)-p-phenetidineの脱エチル化におよぼす尿素誘導体の阻害効果
- 医薬品の生物薬剤学的研究(第6報)o-EthoxybenzamideとN-(β-Hydroxybutyryl)-p-phenetidineの家兎血清中濃度におよぼす2-Bromo-isovalerylureaの併用効果
- 医薬品の吸収, 排泄および代謝に関する研究(第8報)新消炎鎮痛剤2-Oxo-3-[4-(1-oxo-2-isoindolinyl)phenyl]butanamide(OIB)のラットにおける代謝
- 医薬品の生物薬剤学的研究(第3報)併用投与時におけるo-EthoxybenzamideとN-(β-Hydroxybutyryl)-p-phenetidineの血清中動態
- Studies on the Syntheses of Heterocyclic Compounds. CXCV. The Structure of a Yellow Substance formed by Mild Oxidation of Aminopyrine.
- 循環器用剤に関する合成研究(第5報)2-Aminopropiophenone誘導体のAmine Boraneによる立体選択的還元
- 鎮痛剤の合成研究(第55報)4a-(3-Substituted phenyl)-1,2-disubstituted Decahydrocinnoline誘導体の合成 その2(複素環式化合物の合成研究第955報)
- 循環器用剤に関する合成研究(第4報)1位に複素環を有する2-Amino-1-propanone誘導体のSodium Borohydrideによる立体選択的還元(複素環式化合物の合成研究(第852報))
- 鎮痛剤の合成研究(第54報)鎮痛作用を有する3-(Substituted phenyl)-4-oxazolidinoneおよび3-(Substituted phenyl)-3,4,5,6-tetrahydro-2H-1,3-oxazin-4-one誘導体の合成(複素環式化合物の合成研究 第928報)
- 循環器用剤に関する合成研究(第3報)2-(4-Benzylpiperidino)-1-(4-hydroxyphenyl)-propanolの合成およびそのDiastereisomerのConfigurationの決定(複素環式化合物の合成研究第854報)
- 循環器用剤に関する合成研究(第2報)α-Aminopropiophenone誘導体のSodium Borohydrideによる立体選択的還元(複素環式化合物の合成研究第853報)
- 鎮痙剤の合成研究(第4報)2-Cyclohexyl-r-2-phenyl-c-およびt-4-Piperidinomethyl-1,3-dioxolan Methiodideの合成(複素環式化合物の合成研究 第846報)
- 鎮痛剤の合成研究(第53報)3-(4-Substituted phenyl)-2-oxobutanamide誘導体の合成(複素環式化合物の合成研究 第845報)
- 鎮痛剤の合成研究(第52報)4a-(3-Substituted phenyl)-1,2-disubstituted Decahydrocinnoline誘導体の合成(複素環式化合物の合成研究 第843報)
- Synthetic Studies on β-Lactam Antibiotics. XIV. Synthesis of 7H-Azeto [1,2-a] thieno [2,3-c] pyridine Derivatives
- 循環器用剤に関する合成研究(第1報)1-置換3,7-Dimethylxanthine誘導体の合成(複素環式化合物の合成研究第824報)
- 化学療法剤の合成研究(第8報), 1,9b-Dihydro-2H, 4H-2-oxo-azeto[1,2-c][1,3]benzoxazine-4-carboxylic Acid誘導体の立体選択的合成 : 複素環式化合物の合成研究第813報
- 化学療法剤の合成研究(第7報)1,9b-Dihydro-2H, 4H-2-oxo-azeto[1,2-c][1,3]-benzoxazine誘導体の合成(複素環式化合物の合成研究第812報)
- 6-置換 1,2,3,4,4a, 10b-Hexahydro-6H-dibenzo[b, d]pyran誘導体の合成 : 複素環式化合物の合成研究第795報
- 複素環式化合物の合成研究(第776報)N-置換マンデロヒドラジドのホルムアルテヒドによる閉環反応
- 化学療法剤の合成研究(第6報)6-および7-Carbamoyl-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid誘導体の合成 : 複素環式化合物の合成研究第761報
- Studies on the Synthesis of Heterocyclic Compounds. DXIX. A Total Synthesis of (±)-Discretine by Thermolysis
- A Novel Synthesis of Isopavine Ring System
- Studies on the Syntheses of Heterocyclic Compounds. DX. A Novel Rearrangement of proerythrinadienol with Methyl Fluorosulfonate
- Studies on the Syntheses of Heterocyclic Compounds. CDXCIII. Reaction of N-Ethoxycarbonyl-5-methoxytryptamine with Methyl Fluorosulfonate ("Magic Methyl")
- Novel Synthesis of Quinoline Derivatives with Triethyl Phosphite
- The Oxidation of p-Toluidine with Potassium Ferricyanide in Liquid Ammonia
- Benzyne Reaction. II. Syntheses of Benzyl Cyanide Derivatives by Benzyne Reaction (Studies on the Syntheses of Heterocyclic Compounds. CCXLVII)
- Studies on the Syntheses of Heterocyclic Compounds. CCXLV. The Mass Spectra of Cryptaustoline Type Alkaloids
- Studies on the Syntheses of Heterocyclic Compounds. CCXXXVIII. A Modified Synthesis of Pummerer's Ketone
- An Improved Synthesis of Styphnic Acid
- Studies on the Syntheses of Tetracycline Derivatives. III. Synthetic Approach to Adriamycin-Synthesis of the Linear Tetracyclic Skeleton having the Same BC Ring System with Adriamycin
- An Alternative Synthesis of (±)-Dehydrogrisenfulvin by Enzymic Phenolic Oxidation by Homogenized Potato Peelings : Studies on the Syntheses of Heterocyclic Compounds. CCCLIII
- Electrolytic Oxidation. I. Phenolic Oxidation of p-Cresol by Electrolysis (Studies on the Syntheses of Heterocyclic Compounds. CCXXXVII
- Synthesis of Melanthioidine Derivative by Double Ullmann Reaction (Studies on the Syntheses of Heterocyclic Compounds. CCXXVI)
- Chichibabin Reaction. III. Chichibabin Reaction of 7-Methylquinoline and Migration of the Methyl Group in Friedel-Crafts Reaction of N-(m-Tolyl)- and N-(p-Tolyl)-β-chloropropionamide (Studies on the Syntheses of Heterocyclic Compounds. CCXV)
- Studies on the Syntheses of Heterocyclic Compounds. CCIX. Total Syntheses of (±)-Isococlaurine and (-)-Lotusine
- The Nuclear Magnetic Resonance Spectra and Optical Rotatory Dispersion of Berbamunine, Magnoline and Two Diastereoisomers
- An Alternative Synthesis of Stereoisomeric Mixture of Magnoline by Ullmann Reaction (Studies on the Syntheses of Heterocyclic Compounds. CCXLVIII)
- Bisbenzylisoquinoline Alkaloids and Related Compounds. XI. Total Synthesis of Stereoisomeric Mixture of Magnoline
- Bisbenzylisoquinoline Alkaloids and Related Compounds. VI. A Modified Total Synthesis of the Stereoisomeric Mixture of Dauricine
- Capaurimine and Related Compounds. II. Syntheses of Position Isomers of Capaurimine and Capauridine : Studies on the Syntheses of Heterocyclic Compounds. CCCXIII
- An Alternative Synthesis of So-called Corpaverine (Studies on the Syntheses of Heterocyclic Compounds. CCXXXI)
- The Structure of Sendaverine and Its Total Synthesis
- Studies on the Syntheses of Heterocyclic Compounds. DCCLXVIII. Reaction of Pyrrolo [1,2-a] indole Derivatives with N-Bromosuccinimide in Protic Solvents
- Studies on the Syntheses of Heterocyclic Compounds. DCCLV. Iminoketene Cycloaddition. (4). Alternative Syntheses of 5,6,7,8-Tetrahydro-2,3-dimethoxy-8-oxoisoquinolo [1,2-b] quinazoline and Rutecarpine
- Studies on the Syntheses of Heterocyclic Compounds. DCCXXVIII. A Simple Synthesis of 1,3-Benzoxazin-4-ones from Salicylic Acid
- Studies on the Syntheses of Heterocyclic Compounds. DCXCII. A Novel Synthetic Route to Phthalideisoquinoline and Spirobenzylisoquinoline Type Alkaloids
- Studies on the Syntheses of Heterocyclic Compounds. DCXXVI. A Modified Synthesis of Pentazocine
- Studies on the Syntheses of Heterocyclic Compounds. CDLXXXVII. Photolytic Synthesis and Rearrangement of Proerythrinadienones
- Biotransformation of (+)-Reticuline in Rat
- Studies on the Syntheses of Heterocyclic Compounds. CDLII. An Alternative Total Synthesis of Corydalactam
- Studies on the Syntheses of Heterocyclic Compounds. CCCXXI. Synthesis of Isoquinoline Derivatives having Twenty-four Membered Ring System by Ullmann Reaction
- Studies on the Syntheses of Heterocyclic Compounds. DCXLI A Convenient Synthesis of Hexadehydroyohimbine and a Total Synthesis of Yohimbine
- Studies on the Syntheses of Tetracycline Derivatives. I. Thermolytic Cycloaddition of o-Quinodimethanes with Naphthoquinone
- Studies on the Syntheses of Heterocyclic Compounds. DXVI. Total Syntheses of the Aporphine, Morphinandienone, and Tetrahydrodibenzopyrrocoline Alkaloids by Benzyne Reaction
- Total Syntheses of (±)-N-Nordasycarpidone and (±)-Dasycarpidone (Studies on the Syntheses of Heterocyclic Compounds. CDXVIII)
- Dioxolanone関連化合物の合成(第1報) : 3-Aryloxy-1,2-propanediol誘導体の合成について : 複素環式化合物の合成研究 第189報
- 複素環式化合物の合成研究(第752報)アミドアルコールの閉環反応
- Studies on the Syntheses of Heterocyclic Compounds. DXXV. Syntheses of Berberine and Related Compounds. III. Dealkylation of N-Substituted Protoberberinium Salts
- イソヒノリン誘導体及び関連化合物の合成研究(第37報)Heterocyclic Acid Amide又はOximeに対するAllylbenzeneの反応による1-置換3-メチル-3,4-ジヒドロイソヒノリン誘導体の一新製法
- イソヒノリン誘導体及び関連化合物の合成研究(第36報)2'-(p-アミノフェニル)ピリミジノイソヒノリン誘導体の脱アミノ化
- イソヒノリン誘導体及び関連化合物の合成研究(第35報)ピリミジノイソヒノリン類の二重結合転移及び赤外吸収スペクトルによる推定構造
- Studies on the Syntheses of Heterocyclic Compounds. DCCCXCII. An Efficient Stereoselective Synthesis of Potential Intermediates for Rauwolfia Alkaloids from Furan and Its Derivatives
- Studies on the Syntheses of Heterocyclic Compounds. CDXXXIV. The Abnormal Formation of 3-(4-Methoxyphenethyl)-6,7-methylenedioxy-1,2,3-benzotriazin-4-one in Case of Pschorr Reaction
- Aztequine and Related Compounds. IV. A Synthesis of 2,2'-Dihydroxy-4,4'-bis (7-hydroxy-6-methoxy-2-methyl-1,2,3,4-tetrahydro-1-isoquinolylmethyl) diphenyl Ether (Studies on the Syntheses of Heterocyclic Compounds. CCXXX)
- A Novel Dehydrazination Reaction. V. The Formation of Various Amides from Aliphatic and Aromatic Carboxylic Acid Hydrazides in the Presence of Chloral
- A Novel Dehydrazination Reaction
- Studies on the Syntheses of Heterocyclic Compounds. LXII. Synthesis of rac-Tetrahydrorotundine.
- Application of Norphenylephrine Derivatives to the Isoquinoline Syntheses : Studies on the Syntheses of Heterocyclic Compounds. CCCLII
- 3-Oximino-4-oxoisocarbostyrilの還元成績体について : 複素環式化合物の合成研究第293報
- 鎮痛剤の合成研究(第48報)テトラヒドロ-2-ベンズアゼピン誘導体の新しい合成法およびガランタミン関連化合物の合成(複素環式化合物の合成研究(第734報))
- 鎮痛剤の合成研究(第47報) : ガランタミン関連化合物の合成およびアミドアルコールの閉環反応 : 複素環式化合物の合成研究 第708報
- 鎮痙剤の合成研究(第3報)1-Diethylamino-3-hydroxy-2-methylbutaneのジアステレオマーの立体配位について
- 1,2,3,4,4a, 10b-Hexahydro-6H-dibenzo[b, d]pyran誘導体の合成 : 複素環式化合物の合成研究 第652報
- 鎮痛剤の合成研究(第28報) : 4-Amino-3-methyl-1,2-diphenyl-2-propionyloxybutane誘導体の合成
- Phenolic Cyclization. IX. Syntheses of Benz [c] phenanthridine and Related Compounds (Studies on the Syntheses of Heterocyclic Compounds. CDIX)
- 化学療法剤の合成研究(第4報)Pyrazolo[4,3-g]quinoline-6-carboxylic Acid誘導体の合成 : 複素環式化合物の合成研究 第759報
- 化学療法剤の合成研究(第5報)Pyrazolo[4,3-f]および[3,4-f]quinoline-8-carboxylic Acid誘導体の合成 : 複素環式化合物の合成研究第756報
- 鎮痛剤の合成研究(第49報)2-(6-Methoxy-2-naphthyl)propanoic Acidの合成(複素環式化合物の合成研究(第740報))
- Studies on the Syntheses of Analgesics. XLI. Optical Resolution of (±)-N-Cyclopropylmethyl-3-hydroxy-9-azamorphinan (Studies on the Syntheses of Heterocyclic Compounds. Part DCLXIX)
- Phenolic Cyclizationによる1一Carboxy-1,2,3,4-tetrahydroisoquinoline誘導体, 6-Carboxy-1,2,3,4,4a, 5,6,10b-octahydrophenanthridine誘導体および6-Carboxydibenzo[b, d]pyran誘導体の合成(複素環式化合物の合成研究(第664報))
- Studies on the Syntheses of Analgesics. XLVI. An Abnormal Hofmann Degradation of N-(4-Hydroxybenzyl)-3-benzazocinium Halides (Studies on the Syntheses of Heterocyclic Compounds. DCLXVIII)
- Phenolic Cyclizationによる4-Carboxy-1,2,3,4-tetrahydroisoquinoline誘導体の合成(複素環式化合物の合成研究(第643報))
- 鎮痛剤の合成研究(第38報)2-(3-置換フェニル)シクロヘキサノンとα-ハロ)ゲノ酢酸エチルとの反応成績体について(複素環式化合物の合成研究(第532報)
- Benzyne反応(第15報)ハロゲノ安息香酸誘導体と2,3-キシリジンとのBenzyne反応によるメフェナム酸およびその関連化合物の合成
- Studies on the Syntheses of Analgesics. XXXIII. Synthesis of N-Methyl-N-[2-(3-methoxyphenyl)-2-phenyl] propylhydrazine (Studies on the Syntheses of Heterocyclic Compounds. CDXCVI.)
- 鎮痛剤の合成研究(第29報) : N-(2-アミノエチル)-2-インダナミン誘導体の合成と薬理作用
- Synthesis of 1,2,3,4,5,6,7,8-Octahydro-1-(4-methoxybenzyl)-2-methylphthalazine Derivative (Studies on the Syntheses of Heterocyclic Compounds. CDXXXI)
- Phenolic Cyclizationによる1-スピロイソキノリン誘導体の合成 : 複素環式化合物の合成研究 第335報
- Novel Methylation. Methylation of Tertiary Amines with Alkyl Salicylate
- Azamorphinan and Related Compounds. I. A Synthesis of 3-Hydroxy-N-methyl-9-azamorphinan (Studies on the Syntheses of Heterocyclic Compounds. CCXIV)
- Reductive Cyclizationによる4-Oxa-9-aza-9-methyl-6,7-benzobicyclo[3.3.1]nonane合成ならびに本反応によるPiperidone誘導体の還元的閉環の試み : 複素環式化合物の合成研究 第227報
- Reductive Cyclizationによる8-Aza-6-oxa-8-methyl-3,4-benzbicyclo[3,2,1]octaneの合成 : 複素環式化合物の合成研究 第190報
- Phenolic Cyclization. IV. The Mechanism of the Isoquinoline Formation (Studies on the Syntheses of Heterocyclic Compounds. CCCXXXVII)
- ハロゲノベンゼンおよびニトリル間のBenzyne反応によるシアノメチル誘導体の合成とそのイソキノリン合成への応用 : 複素環式化合物の合成研究 第323報
- Reductive Oxygenation(第1報) : 3-Methyl-2,3,4,5,6,7-hexahydro-8H-2,6-methanobenzo[d]-1,3-oxazocineの合成 : 複素環式化合物の合成研究 第180報
- Azabenzomorphan and Related Compounds. X. A Synthesis of 1-Methyl-3-aminoisoquinoline. : (Studies on the Syntheses of Heterocyclic Compounds. CLXXX.)
- Azabenzomorphane and Related Compounds. VII. Synthesis of 1,2,3,4,5,6-Hexahydro-2,6-methanobenzo [d][1,3] diazocine Derivatives
- Azabenzomorphane and Related Compounds. II. A Synthesis of 1,2,3,4-Tetrahydro-6H-1,5-methanobenzo[f][1,4]diazocine