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

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概要

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• Reaction of ⊿^<1,10>-hexahydroquinolizine (I) with trichloroacetic acid in benzene afforded 6-chloro-1-azabicyclo [4. 4. 1] undecan-11-one (II). Acid hydrolysis of II followed by hydrogenation on palladium-charcoal yielded 6-carboxydecahydroazecine (IV), and alkali hydrolysis of II followed by lithium aluminum hydride reduction gave 10-hydroxymethyl-octahydroquinolizine (IX), which was also obtained by lithium aluminum hydride reduction of II. Reaction of II with sodium in liquid ammonia gave both 1-azabicyclo [4. 4. 1] undecan-11-ol (XIII) and 6-carbamoyldecahydroazecine (XIV). The action of p-toluenesulfonyl chloride on the latter compound, followed by reduction with lithium aluminum hydride afforded 1-azabicyclo [4. 4. 1] undecane (XVI).

• 公益社団法人日本薬学会の論文
• 1972-02-25

著者

• 荒田 義雄

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 小林 東洋彦

  Faculty Of Pharmaceutical Sciences Kanazawa University

関連論文

• 1-Azabicyclo化合物の研究(第8報) : Octahydropyrrocolineから9員環状アミンの合成
• Studies on 1-Azabicyclo Compounds. XXVI. Synthesis of Ten-membered Ring Amines from 9a-Cyanomethyl-, 9a-Ethoxycarbonylmethyl-, and 1-Ethoxycarbonyl-octahydroquinolizine
• 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.
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• 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
• 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
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• 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
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• 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
• 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
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• Studies on 1-Azabicyclo Compounds. XI. Syntheses of Ten-membered Ring Amine Derivatives from Di (10-octahydroquinolizinyl)-hydroxylamine
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• Studies on 1-Azabicyclo Compounds. XVII. Transannular Reaction of cis- and trans-1,2,3,4,7,8,9,10-Octahydroazecine and Their Derivatives
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• 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
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