A New Synthesis of 6,7-Benzomorphan

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概要

• 論文の詳細を見る

• A new synthetic route to 6,7-benzomorphan has been developed. 2,2-Dimethyl-7-methoxy-3,4-dihydro-1 (2H)-naphthalenone (1) was cyanomethylated, followed by LiAlH_4 reduction and a Wagner-Meerwein rearrangement, to give aminoethyl compound 3. Treatment of 3 with bromine gave hydrobenz [e] indole 4,which was rearranged to 9-methylene-6,7-benzomorphan 5. Hydrogenation of the methylene gave 5,9α-dimethyl derivative 6,from which 5,9α-dimethyl-2'-hydroxy-6,7-benzomorphan (7) was obtained.

• 公益社団法人日本薬学会の論文
• 1977-05-25

著者

• 三橋 監物

  Faculty of Pharmaceutical Sciences, University of Toyama

• 米谷 正

  富山工業高等専門学校

• 塩谷 俊作

  富山大学教養部

• 米谷 正

  Toyama Technical College

• 二日市 修

  Nihon Iyakuhin Kogyo Co., Ltd.

• 三橋 監物

  Faculty Of Pharmaceutical Sciences Josai University

関連論文

• Studies on Structure-Activity Relationship of Analgetics. XIII. Syntheses of Homobenzomorphans and Related Compounds. (1)
• Heteroaromatic Analogs of Benzomorphan. III. Synthesis of 1,2,3,4,5,6-Hexahydro-2,6-methano-3-methylpyrido [3,2-d] azocine
• Heteroaromatic Analogs of Benzomorphan. II. Synthesis of 2-Azabicyclo-[3.3.1] nonane Derivatives fused to Pyridine Ring. (2)
• Tetrahydronaphthylamines and Related Compounds. III. Synthesis of 1,2,3,4-Tetrahydro-2-naphthylamine and 6-Amino-5,6,7,8-tetrahydroquinoline Derivatives
• Synthesis of 1,2,3,4,5,6-Hexahydro-1,5-methano-2-methylpyrido [2,3-c] azocine
• Thiazole Analogs of Benzomorphans. II. Synthesis of Novel Thiazolo [5,4-f] morphans
• 水溶性切削剤廃液の微生物分解
• Thiazole Analogs of Benzomorphans. I. Synthesis of Novel Thiazolo [4,5-f] morphans
• Heteroaromatic Analogs of Benzomorphan. Synthesis of Novel Thiazolo [4,5-f] morphans
• Tetrahydronaphthylamines and Related Compounds. II. Synthesis of 1,2,3,4-Tetrahydro-6,7-dimethoxy-2-phenyl-2-naphthylamine
• Synthesis of Homobenzomorphans and the Related Compounds. III. 3-Methyl-2,3,4,5,6,7-hexahydro-1,6-methano-1H-3-benzazonine
• On the Cleavage of Tertiary Amines with Ethyl Chloroformate
• Mass Spectral Studies of Aza- and Diazabenzobicycloalkanes. II. Some Aspects of Mass Spectrometry of 1,3-Bridged 1,2,3,4-Tetrahydronaphthalenes, 2,4-Bridged 1,2,3,4-Tetrahydroisoquinolines and 1,3-Bridged 1,2,3,4-Tetrahydroquinolines
• Mass Spectral Studies of Aza-and Diazabenzobicycloalkanes. I. Some Aspects of Mass Spectrometry of 1,3-Bridged 1,2,3,4-Tetrahydroisoquinolines
• Studies on Structure-Activity Relationship of Analgetics. X. Syntheses of 11-Amino-2,3-benzobicyclo [3. 3. 1] nonane and 3-Phenyl-9-amino-bicyclo [3. 3. 1] nonane Derivatives.
• Syntheses of Azabenzobicycloalkanes
• Studies on Diazabenzobicyclo [3.3.1] nonane System. VIII. Synthesis of 8,9-Dimethoxy-11-benzoyl-1,2,5,6-tetrahydro-2,6-imino-3-benzazocin-4 (3H)-one
• Studies on Diazabenzobicyclo [3.3.1] nonane System. VII. Synthesis of 1,2,3,4,5,6-Hexahydro-1,5-methanobenzo [e][1,2] diazocine Derivatives and an Example of Abnormal Cleavage of Hydrazide by Lithium Aluminum Hydride
• Studies on Diazabenzobicyclo [3.3.1] nonane System. VI. Syntheses of 1,2,3,4-Tetrahydro-6H-1,5-methanobenzo [d][1,2] diazocine Derivatives
• Studies on Diazabenzobicyclo-[3.3.1]nonane System. V. Nuclear Magnetic Resonance Spectral Studies on Diazabenzobicyclo[3.3.1]nonane System
• Studies on Diazabenzobicyclo [3.3.1] nonane System. IV. Synthesis of 1,2,3,4,5,6-Hexahydro-1,5-methanobenzo [e] [1,3] diazocine Derivatives
• Studies on Diazabenzobicyclo [3.3.1] nonane System. I. Syntheses of 3,4,5,6-Tetrahydro-2H-1,5-methanobenzo [g]-[1,4] diazocine and its Derivatives.
• N-Alkyl-10-hydroxy-2,3,4,5,6,7-hexahydro-1,6-methano-1H-4-benzazonine誘導体の合成
• 新鎮痛剤(-)-1,4-Dimethyl-10-hydroxy-2,3,4,5,6,7-hexahydro-1,6-methano-1H-4-benzazonine Hydrobromide(l-ST-2121)のラット尿中代謝産物の合成とその鎮痛作用
• A New Synthesis of 6,7-Benzomorphan
• Synthesis of 1,3-Bridged 1,2,3,4,5,6-Hexahydro-2,6-methano-3-benzazocine Derivatives
• Synthesis of 3-Carboxymethyl-I-(N-methylaminomethyl)indane and Its Ester
• On the Cleavage of Tertiary Amines with Ethyl Chloroformate
• Reaction of Alkyl Dialkoxyphosphinyl Formate with Strong Base
• Studies on Structure-Activity Relationship of Analgetics. XVII. Syntheses of Homobenzomorphans and Related Compounds.(2)
• Synthesis of 9-Amino-3,6-dimethy1-8-methoxy-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine
• 3-Methyl-2,3,4,5,6,7-hexahydro-2,7-methano-1H-3-benzazonine の一新合成法について
• The Reaction of α, β-Unsaturated Ketones with Azides. III.
• Sodium Borohydride Reduction of α-Functionalized Ester
• 液体クロマトグラフ質量分析計(JMS-AX500)
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• 酵母による光学活性アルコール類製造のためのリアクターに関する研究
• An Esterification Procedure Using N-Hydroxysuccinimidyl Esters
• ピラノ・ナフトキノン系抗生物質の合成
• Thiazole Analogs of Benzomorphans. III. Syntheses of 4,5,6,7,8,9-Hexahydro-4,8-methano-5-methylthiazolo [4,5-c] azocine and 4,5,6,7,8,9-Hexahydro-4,8-methano-5-methylthiazolo [5,4-c] azocine
• Reaction of Conjugated Dienones with Hydrazoic Acid
• The Reaction of α, β-Unsaturated Cycloalkenones with Azides. I. The Anomalous Products in the Schmidt Reaction

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