Studies on Heterocyclic Enaminonitriles. I. Synthesis and Aromatization of 2-Amino-3-cyano-1-ethoxycarbonyl-4,5-dihydropyrroles

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概要

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• The reaction of 1-ethoxycarbonylaziridine with malononitrile in the presence of sodium hydride gave 2-amino-3-cyano-1-ethoxycarbonyl-4,5-dihydropyrrole (IIa) in 47% yield. Similarly, 1-ethoxycarbonyl-2-methyl (or phenyl) aziridine reacted with malononitrile to give 2-amino-3-cyano-5-methyl (or 4-phenyl)-4,5-dihydropyrrole (IIb or c). Compounds IIa-c were dehydrogenated to the corresponding pyrroles (IVa-c) when heated with chloranil in benzene. 2-Amino-3-cyano-1-ethoxycarbonyl-4-phenylpyrrole (IVc) was also synthesized from ethyl N-phenacylcarbamate and malononitrile. The 2-benzamido derivatives of IIa-c reacted with N-bromosuccinimide in the presence of 2,2'-azobisisobutyronitrile to produce the corresponding 2-benzamido-3-cyano-1-ethoxycarbonylpyrroles (Va-c) as major products.

• 社団法人日本薬学会の論文
• 1982-07-25

著者

• 園田 美樹

  Faculty Of Pharmaceutical Sciences Fukuoka University

• 冨岡 幸彦

  Faculty Of Pharmaceutical Sciences Fukuoka University

• 山崎 企善

  Faculty of Pharmaceutical Sciences, Fukuoka University

• 栗山 伸隆

  Faculty of Pharmaceutical Sciences, Fukuoka University

• 山崎 企善

  Faculty Of Pharmaceutical Sciences Fukuoka University

• 栗山 伸隆

  Faculty Of Pharmaceutical Sciences Fukuoka University

関連論文

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• Studies on Heterocyclic Enaminonitriles. VII. : Reactions of 2-Amino-3-cyano-4,5-dihydrothiophenes with Acetylenic Esters
• Studies on Heterocyclic Enaminonitriles. V. Reactions of 2-Amino-3-cyano-1-ethoxycarbonyl-4,5-dihydropyrroles with Acetylenic Esters
• Studies on Heterocyclic Enaminonitriles. X. : Synthesis of 4-Amino-7-ethoxycarbonyl-5,6-dihydro-7H-pyrrolo-[2,3-d]pyrimidine-2-acetic Acid Derivatives
• Studies on Heterocyclic Enaminonitriles. I. Synthesis and Aromatization of 2-Amino-3-cyano-1-ethoxycarbonyl-4,5-dihydropyrroles
• Studies on Heterocyclic Enaminonitriles. IV. Reaction of Ethyl N-(3-Cyano-4,5-dihydro-2-thienyl) oxamates with Cyanomethylene Compounds in the Presence of Triethylamine
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• Studies on Tertiary Amine Oxides. X. Alkaline Ferricyanide Oxidation of Some Aromatic N-Oxides.
• Bromination of Pyridine and Quinoline 1-Oxides

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