Studies on 1-Azabicyclo Compounds. VII. Syntheses of Ten-membered Ring Amines from Octahydroquinolizine

スポンサーリンク

概要

• 論文の詳細を見る

• 10-Cyano-5-methyloctahydroquinolizinium iodide (V) was treated with silver oxide to give carbamoyl methohydroxide (VI), which was further converted to carbamoyl methobromide (VII). Reaction of V and VII with lithium in liquid ammonia afforded 1-methylazecane (IX) and 10-cyano-1-methylazecane (VIII), and 1-methylazecane-6-carboxamide (XI) and a demethylated compound (IX), respectively. 10-Amino-5-methyloctahydroquinolizinium bromide (XIV) which was derived from VII was heated in an alkaline solution affording 1-methyl-6-azecanone (XV), whose ring appears in the majority of the medium sized ring alkaloids.

• 公益社団法人日本薬学会の論文
• 1969-07-25

著者

• 吉藤 茂行

  Faculty of Pharmaceutical Sciences, Hokuriku University

• 荒田 義雄

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 吉藤 茂行

  Faculty Of Pharmaceutical Sciences Of Hokuriku University

• 吉藤 茂行

  金沢大学薬学部

• 安田 義弘

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 安田 義弘

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 吉藤 茂行

  Faculty Of Pharmaceutical Sciences Hokuriku University

関連論文

• Structure-Activity Relationships of Diamines, Dicarboxamides, and Disulfonamides on Vinblastine Accumulation in P388/ADR Cells
• Lactam類, Pyridone類, ならびに関連化合物74種の抗腫瘍性について
• 1-Azabicyclo化合物の研究(第8報) : Octahydropyrrocolineから9員環状アミンの合成
• Quinolizidines. VIII. Structure and Synthesis of the Alangium Alkaloid Alangicine : Syntheses of (±)- and (+)-Alangicines
• Lactams. XIII. Alkylation of Lactim Ethers : A Novel Synthetic Route to N-(2-Arylethyl) lactams from N-Unsubstituted Lactams
• Studies on 1-Azabicyclo Compounds. XXVI. Synthesis of Ten-membered Ring Amines from 9a-Cyanomethyl-, 9a-Ethoxycarbonylmethyl-, and 1-Ethoxycarbonyl-octahydroquinolizine
• A New Method for the Synthesis of Amides from Amines : Ruthenium Tetroxide Oxidation of N-Protected Alkylamines
• Chemical Conversion of L-α,ω-Diamino Acids to L-ω-Carbamoyl-α-amino Acids by Ruthenium Tetroxide Oxidation(Organic,Chemical)
• Ruthenium Tetroxide Oxidation of N-Acylated Alkylamines: A New General Syuthesis of Imides(Organic,Chemical)
• A New Approach for the Total Synthesis of L-γ-Carboxyglutamic Acid : Utility of Ruthenium Tetroxide Oxidation
• A Novel Synthesis of L-Pyroglutamic Acid Derivatives from L-Proline : Utility of N-Protecting Groups for Ruthenium Tetroxide Oxidation of Cyclic α-Amino Acids
• Chemical Conversion of Cyclic α-Amino Acids to α-Aminodicarboxylic Acids by Improved Ruthenium Tetroxide Oxidation
• A NOVEL SYNTHESIS OF L-ω-CARBAMOYL-α-AMINO ACIDS FROM L-α, ω-DIAMINO ACIDS BY RUTHENIUM TETROXIDE OXIDATION METHOD
• Studies on 1-Azabicyclo Compounds. XXVIII. Synthesis of 1-Methyl-perhydroazocin-5-one from Pyrrolizidine
• Synthesis of (±)-Methyldecamine
• 双環状アミン体から中環状アミン類の合成
• Synthetic Studies on Lythraceae Alkaloids. V. Total Synthesis of (±)-Vertaline
• Synthetic Studies on Lythraceae Alkaloids. IV. Total Synthesis of (±)-Methyldecinine
• Total Synthesis of (±)-Lagerine
• Synthetic Studies on Lythraceae Alkaloids. III. Stereoselective Total Synthesis of (±)-Decaline
• Synthetic Studies on Lythraceae Alkaloids. II. The Mannich Reaction of Isopelletierine with 3-Methoxybenzaldehyde and 3-Hydroxybenzaldehyde
• Studies on 1-Azabicyclo Compounds. XXIV. Synthesis and Stereochemistry of 10-Ethyl-, 10-Vinyl-, and 10-Ethynyl-quinolizidine Methiodides
• Studies on 1-Azabicyclo Compounds. XXII. Stereochemistry of 9a-Substituted Quinolizidine Methiodides
• Studies on 1-Azabicyclo Compounds. XIX. Synthesis of Ten-membered Ring Amine Derivatives from 5-Methyl-10-nitromethyloctahydro-quinolizinium Iodide and Its Derivatives
• Studies on 1-Azabicyclo Compounds. XIV. Synthesis of 1-Methyldecahydro-1,4-diazecin-5-one from Octahydropyrido [1,2-a] pyrazine Derivatives
• Studies on 1-Azabicyclo Compounds. XIII. Synthesis of 1-Methyl-6-decahydroazecinone by the Reaction of 3,4,6,7,8,9-Hexahydro-2H-quinolizine with Methyl Iodide
• Syntheses of Ten-membered Ring Amine Derivatives and 1-Azabicyclo-[4,4,1] undecane from 3,4,6,7,8,9-Hexahydro-2H-quinolizine
• Constituents of Rhizoma Nupharis. XXI. Structure of Dehydro-deoxynupharidine
• Dehydro-deoxynupharidine : A New Alkaloid of Nuphar japonicum DC
• Constituents of Rhizoma Nupharis. XVIII. Synthesis of Alkaloids from Nuphar japonicum DC. I. Synthesis of rac-Deoxynupharidine.
• Lactams. VII. Stereochemical Characterization and Cis-Trans Isomerization of 5-Ethyl-2-oxo-4-piperidineacetic Acid and Related Compounds
• Lactams. XVII. Synthesis and Stereochemical Characterization of Diethyl cis-and trans-5-Ethyl-2-oxo-4-piperidinemalonate
• Latams. X. The Alkaline Ferricyanide Oxidation of 3-Substituted 1-(3,4-Dimethoxyphenethyl) pyridinium Salts : Effects of Functional Substituents
• Lactams. VIII. The Alkaline Ferricyanide Oxidation of 3-Substituted 1-(3,4-Dimethoxyphenethyl) pyridinium Salts : Effects of Hydrocarbon Substituents on Orientation of the Oxidation
• Lactams. VI. Synthesis and Nuclear Magnetic Resonance Study of 1-Aralkyl-3-methyl- and -5-methyl-2(1H)-pyridones
• 1-Azabicyclo化合物の研究(第9報) : 3,4,6,7,8,9-Hexahydro-2H-quinolizineとRNH_2誘導体の縮合反応(有機化学)
• Studies on 1-Azabicyclo Compounds. VII. Syntheses of Ten-membered Ring Amines from Octahydroquinolizine
• Syntheses of Ten-membered Ring Amines from Quinolizidine
• Constituents of Rhizoma Nupharis. XXVIII. New Syntheses of (±)-7-Epideoxynupharidine, (±)-1-Epi-7-epideoxynupharidine, (±)-Deoxynupharidine, and (±)-1-Epideoxynupharidine
• Constituents of Rhizoma Nupharis. XXVII. Synthesis and Stereochemistry of 1- and 7-Methyl-4-phenylquinolizidin-2-one
• Constituents of Rhizoma Nupharis. XXVI. Carbon-13 Nuclear Magnetic Resonance Spectra of Nupharamine, Anhydronupharamine, Nuphamine, and Related Compounds
• Studies on the Stability of Amides. I. Hydrolysis Mechanism of N-Substituted Aliphatic Amides
• 26 Lythraceaeアルカロイドの合成 : (±)-Decaline,(±)-Vertaline,(±)-Desmethyldecaline,(±)-Methyldecinine,(±)-Methyllagerineの全合成
• 1-Azabicyclo 化合物の研究 (第23報) Deoxynupharidine の酢酸水銀酸化について
• Studies on 1-Azabicyclo Compounds. XII. Synthesis of 5,6,8,9,10,11,11a, 12-Octahydroindolo [3,2-b] quinolizine and Related Compounds
• Constituents of Rhizoma Nupharis. XXV. Formation of Dehydro-deoxynupharidine from Nupharidine
• 川骨成分の研究(第24報) : 新アルカロイド Anhydronupharamine について
• Asymmetric Synthesis of Lycoperdic Acid
• Synthesis of Conformationally Defined Glutamic Acid Analogues from Readily Available Diels-Alder Adducts
• Stereospecific Synthesis of (R)- and (S)-Baclofen and (R)- and (S)-PCPGABA [4-Amino-2-(4-chlorophenyl)butyric Acid]via (R)- and (S)-3-(4-Chlorophenyl)pyrrolidines
• STEREOSPECIFIC SYNTHESIS OF MESO-DIAMINODICARBOXYLIC ACIDS
• Synthesis of (3S, 4S)-3,4-Dihydroxyprolines from L-Tartaric Acid
• Ruthenium Tetroxide Oxidation of 3,4-Dihydroisoquinolin-1(2H)-ones : An Efficient Synthesis of Isoquinoline-1,3,4(2H)-triones
• Quinolizidines. XXV. : An Extension of the "Lactim Ether Route" to the Racemic Syntheses of Several Indolo[2,3-α]quinolizidine Alkaloids
• Ruthenium Tetroxide Oxidation of N-Alkyllactams(Organic,Chemical)
• Quinolizidines. XVIII. Synthesis of (-)- and (+)-ankorines through a lactim ether route
• Ruthenium Tetroxide Oxidation of 1-Azabicycloalkan-2-ones
• Quinolizidines. XIII. Syntheses of (±)-and (-)-Alangimarckines
• Lactams. XXIII. Thermal cis-trans isomerization of the 5-ethyl-2-oxo-4-piperidineacetic acid system: Effect of an N-substituent
• 1-Azabicyclo化合物の研究(第21報)1,2,3,10,11,11a-Hexahydro-5H-pyrrolo-[2,1-c][1,4]benzodiazepin-11-oneおよび5,6,6a, 7,8,9,10,12-Octahydropyrido[2,1-c][1,4]benzodiazepin-6-oneから中環状AminolactamおよびSpiroaminolactam体の合成
• Synthesis of (±)-Desmethyldecaline
• Synthesis of the Compound proposed as the Structure of Lagerine and Its Non identity with Lagerine
• Synthesis of (±)-Methyldecinine
• Lythraceaeアルカロイドの合成研究(第1報)Isopelletierineの一改良合成
• Total Synthesis of (±)-Vertaline
• Studies on 1-Azabicyclo Compounds. XVIII. Synthesis of Fourteenmembered Ring Diamine, 1,8-Dimethyl-1,8-diazacyclotetradecane, and Related Compounds from Perhydrodipyrido [1,2-a : 1', 2'-d]-pyrazine via Ten-membered Ring Diamine, 2-Methyl-perhydro-2H-pyrid
• Studies on 1-Azabicyclo Compounds. XVI. Synthesis of 1'-Methylindan-2-spiro-2'-piperazine and Related Compounds
• Studies on 1-Azabicyclo Compounds. XV. Oxidation of 1,3,4,6,11,11a-Hexahydro-2H-pyrazino [1,2-b] isoquinolin-1-one Derivatives with Mercuric Acetate, and Their Conversion into 1,2,3,4,5,6,7,8-Octahydro-2-methyl-2,5-benzodiazecine and Related Compounds
• 有機硫黄化合物の研究(第3報)cis-およびtrans-1-Thioniabicyclo-[4.4.0]decane Bromideの反応
• 有機硫黄化合物の研究cis-およびtrans-1-Thioniabicyclo[4.4.0]-decane Bromideの分離および反応
• Constituents of Rhizoma Nupharis. XXIII. The Absolute Configuration of Nuphamine
• Constituents of Rhizoma nupharis. XXII. Structure of Nuphamine
• Nuphamine : A New Alkaloid of Nuphar japonicum DC
• Studies on 1-Azabicyclo Compounds. XXVII. Synthesis of Ten-membered Ring Amines from 1-Oxo-, 9a-Benzyl-, and 9a-Benzyl-1-oxo-quinolizidine
• Chemical Transformation of Protoberberines. III. Convenient Synthesis of 8-Methoxyberberinephenolbetaine by Photooxygenation of Berberine. A Novel Conversion of Berberine into (±)-Ophiocarpine, (±)-Epiophiocarpine, (±)-α-Hydrastine, and (±)-β-Hydrastine
• Chemical Transformation of Protoberberines. I. Conversion of Tetrahydroberberine and Dihydroberberine into Noroxyhydrastinine by Photooxygenation
• 53 Berberine及びその誘導体の光酸素化反応と関連アルカロイドへの変換
• Quinolizidines. I. : Quaternization of the Quinolizidine System : Effect of β, γ-Unsaturation on Stereoselectivity in Methiodide Formation
• 1-Azabicyclo化合物の研究 その6 : Octahydroquinolizineの1改良合成法ならびにその脱水素化反応について
• Studies on 1-Azabicyclo Compounds. X. Syntheses of Ten-membered Ring Amine Derivatives and 1-Azabicyclo [4. 4. 1] undecane from 3,4,6,7,8,9-Hexahydro-2H-quinolizine
• Studies on 1-Azabicyclo Compounds. XI. Syntheses of Ten-membered Ring Amine Derivatives from Di (10-octahydroquinolizinyl)-hydroxylamine
• 1-Azabicyclo化合物の研究その5 : 4-Oxoquinolizidineの水素化リチウムアルミニウム還元およびQuinolizidineの酢酸第二水銀酸化により得られた二量体の化学構造
• Lactams. V. Syntheses of 1-(2-Arylethyl)-3-alkyl-2- and -6-piperidones : A Comparative Study of the Mercuric Acetate-EDTA and the Ferricyanide Oxidation Methods
• Studies on 1-Azabicyclo Compounds. XVII. Transannular Reaction of cis- and trans-1,2,3,4,7,8,9,10-Octahydroazecine and Their Derivatives
• Lactams. XV. Chemistry of Unsaturated δ-Valerolactams
• Synthesis of 3-tert-Butylpyridine
• 双環状アミン体から中環状アミン類の合成
• Quinolizidines. III. An Improved Synthetic Route to Stereoisomers of dl-2,3-cis-Emetine
• Quinolizidines. II. A Stereoselective Synthesis of Emetine
• Preparation of Some Ring-Oxygenated Phenacyl Bromides
• Lactams. XIV. cis-trans Isomerization in the 5-Ethyl-2-oxo-4-piperidineacetic Acid System under Fischer-Speier Esterification Conditions
• Lactams. XII. Improvements in the Synthesis of Ethyl trans-5-Ethyl-2-oxo-4-piperidineacetate
• Lactams. XI. Construction of Lactam Carbonyl Function in 1,3-Disubstituted Piperidines by Mercuric Acetate-EDTA Oxidation : Effects of Carbonyl and Related Groups at the 3-Position
• Lactams. IX. Generation of Lactam Carbonyl Function in 1,3-Disubstituted Piperidines by Mercuric Acetate-EDTA Oxidation : Effects of Hydrocarbon Substituents at the 3-Position
• 42 AlangiumアルカロイドAnkorineの構造と絶対配置 : (±)-Ankorineの全合成およびキナアルカロイドとの化学的相互関連
• Deoxynupharidine誘導体の合成
• 3-(5-Nitro-2-furyl)-benzo-1,2,4-triazine誘導体の合成ならびに抗細菌作用について
• N-アシルアミン類および関連化合物の四酸化ルテニウム酸化
• 1-Azabicyclo化合物の研究(第20報)Hexahydroisoquino[3,2-c][1,4]benzodiazepineおよび関連化合物の合成ならびにHexahydroisoquino[3,2-c]-[1,4]benzodiazepin-13-one から6-Methyl-hexahydro-5H-dibenzo[b, g][1,5]diazacycloundecineの生成

もっと見る 閉じる

スポンサーリンク