Benzylcarbonyl 化合物とFormamideとの反応(第2報) : Isoquinoline誘導体の新合成法

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概要

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• Treatment 3,5-dimethoxyphenylacetonitrile(II) with (CH_3)_2NCHO and POCl_3 under the usual conditions of the Vilsmeier reaction gave 3-chloro-6,8-dimethoxyisoquinoline(IV). Although IV had already been synthesized from II by the Gattermann reaction, ^<4)>its formation from II by the Vilsmeier reaction has not been described. Under the conditions of the Vilsmeier reaction only modified by using H_2NCHO in place of (CH_3)_2NCHO, 2-(3,5-dimethoxyphenyl)-5-(4-methoxyphenyl)-3-oxopentanonitrile (V) gave 4-isoquinolinecarbonitriles(VI and VII). The formation of VII may proceed through the elimination of the acyl group, since 4-methoxydihydrocinnamamide (VIII) was isolated from the reaction mixture. Several other α-acyl-3,5-dimethoxyphenylacetonitriles (IXa, b, c, and d) were used to generalize this direct isoquinoline synthesis, and the corresponding 4-isoquinolinecarbonitriles(Xa, b, c, and d) were obtained without any acyl group elimination. In the case of IXa and IXd, enamines(XIa and XId) were also isolated as by-products.

• 公益社団法人日本薬学会の論文
• 1969-11-25

著者

• 廣田 喬

  Faculty Of Pharmaceutical Sciences Okayama University

• 大和 正利

  第一薬科大学

• 小山 鷹二

  熊本大学薬学部

• 戸田 睦子

  熊本大学薬学部

• 廣田 喬

  熊本大学薬学部

• 伊藤 逸也

  熊本大学薬学部

関連論文

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• Reaction of Benzoxazoline-2-thiones with Alkyl Halides
• Polycyclic N-Hetero Compounds. VI. Synthesis of 11,13,15-Triazasteroidal Compounds and Correction of the Structures of Its Intermediates
• Polycyclic N-Hetero Compounds. II, Synthesis of 11,13,15-Triazasteroidal Skeleton
• Syntheses of 3-Substituted 1-Methyl-6-phenylpyrimido[5,4-e]-1,2,4-triazine-5,7(1H, 6H)-diones (6-Phenyl Analogs of Toxoflavin) and Their 4-Oxides, and Evaluation of Antimicrobial Activity of Toxoflavins and Their Analogs
• Polycyclic N-Hetero Compounds. XVI. Reactions of Benzyl Ketones with Formamide or Acetamide
• Benzylcarbonyl化合物とFormamideとの反応.VIII.m-位にMethyl基を有するα-Acylphenylacetonitrileの反応
• Polycyclic N-Hetero Compounds. VIII. Reactions of Ketones with Trisformylaminomethane
• Polycyclic N-Hetero Compounds. VII. Reactions of Benzyl Ketones with Formamide XI
• Polycyclic N-Hetero Compounds. XVII. Reactions of Heterocyclic Active Methyl Group with Formamide or Trisformylaminomethane
• Polycyclic N-Hetero Compounds. XV. The Vilsmeier Reaction of Phenylacetonitriles. II
• Polycyclic N-Hetero Compounds. IV. Reactions of 4-Amino-5-arylpyrimidines with Dimethyl Sulfoxide
• Benzylcarbonyl化合物とFormamideとの反応(第9報)α-Acyl-5,6,7,8-tetrahydro-2-naphthylacetonitrileとの反応
• Benzylcarbonyl化合物とFormamideとの反応(第10報)α-Acyl-α-naphthylacetonitrileとの反応
• 1,3,10-Triazaphenanthreneの合成(第1報)
• Benzylcarbonyl化合物とFormamideとの反応(第7報) : Desoxybenzoinの反応
• Benzylcarbonyl化合物とFormamideとの反応(第6報) : Isoquinoline誘導体の生成
• Benzylcarbonyl化合物とFormamideとの反応(第5報) : α-Acyl-3,4-dimethoxyphenylacetonitrileとの反応
• Benzylcarbonyl化合物とFormamideとの反応(第4報)
• Benzylcarbonyl 化合物とFormamideとの反応(第2報) : Isoquinoline誘導体の新合成法
• Benzylcarbonyl化合物とFormamideとの反応(第3報)
• Polycyclic N-Hetero Compounds. XIV. Reactions of Methylpyridines with Formamide
• Polycyclic N-Hetero Compounds. XIII. Reactions of Pyridine N-Oxides with Formamide
• Polycyclic N-Hetero Compounds. XII. Reactions of Dihydroxynaphthalenes with Formamide or Trisformylaminomethane
• Polycyclic N-Hetero Compounds. XI. The Modified Vilsmeier Reaction of 4-Alkylpyrimidines
• Polycyclic N-Hetero Compounds. X. Reactions of 1,3-Cyclohexanedione and Its Dimer with Formamide or Trisformylaminomethane
• Polycyclic N-Hetero Compounds. IX. Reactions of Tetralones with Formamide or Trisformylaminomethane
• Polycyclic N-Hetero Compounds. XXIV. : Reaction of Pyridine and Quinoline N-Oxides with N-Methylformamide
• Polycyclic N-Hetero Compounds. XVIII. Synthesis of the 11,13,15-Triazasteroidal Skeleton with an Oxygen Function at C-17
• Polycyclic N-Hetero Compounds. V. A Novel Synthesis of Isoquinoline by the Vilsmeier Reaction of Phenylacetonitriles
• Polycyclic N-Hetero Compounds. III. Synthesis of 1,3,10-Triazaphenanthrenes
• Polycyclic N-Hetero Compounds. XXIII. : Synthesis and Antidepressive Activity of 4-Substituted 5,6-Dihydrobenzo[h]quinazolines
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