Pyrrolo[1,2-α]indole誘導体の合成

スポンサーリンク

概要

• 論文の詳細を見る

• By treatment with acetic anhydride and acetic acid, 1-(2-carboxyphenyl)-3,4-dimethylpyrroles (1) gave 1,2-dimethyl-9H-pyrrolo[1,2-α]indol-9-ones (2) in a good yield. 3-Cyano derivatives (4) were synthesized by bromination of 2 with bromine or N-bromosuccinimide to 3-bromo derivatives (3) followed by treatment of the latter with cuprous cyanide. Hydrolysis of 4 gave 1,2-dimethyl-9-oxo-9H-pyrrolo[1,2-α]indole-3-carboxylic acids (5) and the rearranged products, whose structure was assumed as 8,9-dimethyl-7-hydroxy-6,10-dihydropyrido[1,2-α]indole-6,10-diones (6) on the basis of the spectroscopic properties. The ratio of the products 5/6 varied with the position of chloro group on the phenyl ring. Hydrolysis of 3 with aqueous potassium hydroxide yielded 1,2-dimethyl-9-hydroxy-3H-pyrrolo[1,2-α]indol-3-ones (11). The same product 11e was also obtained by oxidation of 2e with lead tetraacetate.

• 公益社団法人日本薬学会の論文
• 1974-02-25

著者

• 川松 豊

  干寿製薬株式会社経営戦略室

• 杉原 弘貞

  武田薬品中央研究所化学研究所

• 杉原 弘貞

  Central Research Division Takeda Chemical Industries. Ltd.

• 松本 憲親

  武田薬品中央研究所 化学研究所

• 川松 豊

  武田薬品中央研究所, 化学研究所

関連論文

• Synthesis and Angiotensin Converting Enzyme-Inhibitory Activity of 1,5-Benzothiazepine and 1,5-Benzoxazepine Derivatives. III
• Synthesis and Angiotensin converting Enzyme Inhibitory Activity of 1,5-Benzothiazepine and 1,5-Benzoxazepine Derivatives. II
• Synthesis and Angiotensin Converting Enzyme Inhibitory Activity of 1,5-Benzothiazepine and 1,5-Benzoxazepine Derivatives. I
• 1,5-Benzoxathiepin Derivatives. II. Synthesis and Serotonin S_2-Receptor-BIocking Activity of Aminoalkyl-Substituted 3,4-Dihydro-2H-1,5-benzoxathiepin-3-ols and Related Compounds(Medicinal Chemistry,Chemical)
• 1,5-Benzoxathiepin Derivatives. I. Synthesis and Reaction of 1,5-Benzoxathiepin Derivatives(Medicinal Chemistry,Chemical)
• インスリン抵抗性改善薬ピオグリタゾンの創製
• Studies on Antidiabetic Agents. VII. : Synthesis and Hypoglycemic Activity of 4-Oxazoleacetic Acid Derivatives
• Studies on Antidiabetic Agents. II. Synthesis of 5-[4-(1-Methylcyclohexylmethoxy)-benzyl] thiazolidine-2,4-dione (ADD-3878) and Its Derivatives
• Studies on Antidiabetic Agents. I. Synthesis of 5-[4-(2-Methyl-2-phenylpropoxy)-benzyl] thiazolidine-2,4-dione (AL-321) and Related Compounds
• Syntheses and β-Adrenoceptor Activities of 2-Alkylamino-6-hydroxy-5-hydroxymethyl-1,2,3,4-tetrahydro-1-naphthalenols
• The Syntheses and β-Adrenoceptor Activities of N-Substituted 2-Amino-5,6-dihydroxy-1,2,3,4-tetrahydro-1-naphthalenols
• 1-Aryl-1-acetoxy-3-buteneのフラシュ熱閉環反応(第1報)
• New 1,4-Dihydropyridine Derivatives with Potent and Long-Lasting Hypotensive Effect
• Studies on Antidiabetic Agents. VI. Asymmetric Transformation of (±)-5-[4-(1-Methylcyclohexylmethoxy) benzyl]-2,4-thiazolidinedione (Ciglitazone) with Optically Active 1-Phenylethylamines
• Studies on Antidiabetic Agents. IV. Synthesis and Activity of the Metabolites of 5-[4-(1-Methylcyclohexylmethoxy) benzyl]-2,4-thiazolidinedione (Ciglitazone)
• Antiulcer Activity of 5-Benzylthiazolidine-2,4-dione Derivatives
• Studies on Antidiabetic Agents. III. 5-Arylthiazolidine-2,4-diones as Potent Aldose Reductase Inhibitors
• Syntheses of 6-Amino-1,2-dihydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol Derivatives
• Syntheses of 1,2-N-Alkylimino-1,2,3,4-tetrahydronaphthalene Derivatives and Preparation of Ring Closed Analog of Salbutamol as a New β-Adrenoceptor Agent
• Spirocyclopropane Compounds. III. Synthesis of Spiro [benzofuran-2 (3H), 1'-cyclopropan]-3-ones for Evaluation as Gastric Antisecretory and Antiulcer Agents
• Chemistry of Salicylic Acid and Anthranilic Acid. I. Reduction of Methyl Salicylate, Methyl Anthranilate and Their Derivatives with Sodium Borohydride
• Chemistry of Salicylic Acid and Anthranilic Acid. II. Formation of 2-Alkyl-3-(2-carboxyphenyl)-4-quinazolone from 2-Alkyl-4-oxo-4H-3,1-benzoxazine by Dimeric Condensation
• Decomposition of Thiamine in Alcohol Solution. II
• Pyrrolo[1,2-α]indole誘導体の合成
• Studies on the Syntheses of N-Heterocyclic Compounds. VII. 2-Aryl-5,8-disubstitutedpyrimido [4,5-d] pyridazine
• Studies on the Syntheses of N-Heterocyclic Compounds. V. 2-Aryl-5,8-dichloropyrimido [4,5-d] pyridazine
• 含窒素複素環式化合物の合成研究(第12報)Pyrido[3,4-d]pyridazineおよびPyrido[2,3-d]pyridazine誘導体の合成
• Syntheses of conformationally Rigid Catecholamine Derivatives
• Spirocyclopropane Compounds. VI. : Synthesis of Spiro[benzo[b]-thiophene-2(3H), 1'-cyclopropan]-3-ones
• Stereoselective Syntheses of cis- and trans-2-Alkylamino-1,2,3,4-tetrahydro-1-naphthalenols by Acid-catalyzed Ring Opening of 1,2-N-Alkylimino-1,2,3,4-tetrahydronaphthalenes
• 14 イソプレノイドキノン類の合成
• Sterische Struktur der Giftstoffe aus dem Fruchtfleisch von Ginkgo biloba L.
• An Improved Synthesis of the New Angiotensin Converting Enzyme Inhibitor CV-5975 via a Chemoenzymatic Process(Organic,Chemical)

もっと見る 閉じる

スポンサーリンク