Synthesis of 2-(1-azulenyl)ethanamine derivatives by aminoethylation of azulenes with aziridines.

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概要

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• Azulene analogs of biological active amines were synthesized. Reaction of azulene or guaiazulene with 1-butanoylaziridine or with 1-butanoyl-2-methylaziridine in the presence of Lewis acid catalyst formed the corresponding <I>N</I>-butanoyl-1-(1-azulenyl)-, <I>N</I>-butanoyl-2-(1-azulenyl)-, and <I>N</I>-butanoyl-2-(1-guaiazulenyl) derivatives of ethanamine, or 1-propanamine, or of 2-propanamine, respectively (<B>5</B>–<B>9</B>). Reaction of guaiazulene with 2-methyl-, or 1,1-dimethylaziridinium, or with 1,1,2,2-tetramethylaziridinium ions gave the corresponding 1-(1-guaiazulenyl)- and 2-(1-guaiazulenyl) derivatives of ethanamine, or 1-propanamine, or of 2-propanamine. 2-(1-Azulenyl)- and 2-(4,6,8-trimethyl-1-azulenyl) derivatives of ethanamine were also obtained by the action of 1,1-diethylaziridinium ion on azulene or on 4,6,8-trimethylazulene. Compounds <B>5</B>, <B>6</B>, and <B>9</B> were active <I>in vitro</I> in the inhibition of prostaglandin 15-hydroxydehydrogenase and of cyclic AMP-phosphodiesterase.

• 公益社団法人 日本化学会の論文

著者

• Anderson Jr.

  Department of Chemistry, University of Washington

• Kurokawa Shinji

  Department of Chemistry, Faculty of Education, Saga University

関連論文

• Synthesis of 4,8-dimethyl-5,7-nonamethyleneazulene.
• Thermolysis of phenyl 3-guaiazulenecarboxyate and the p-acetyl and p-methoxy derivatives.
• Synthesis of 2-(1-azulenyl)ethanamine derivatives by aminoethylation of azulenes with aziridines.
• The Thermal Reaction of 3-Formylguaiazulene
• The Thermal Reaction of 3-Acetylguaiazulene with Sulfur
• Synthesis of 2-(4-azulenyl)ethanamine derivatives as a nonbenzenoid analog of biogenic amine.
• The Thermal Reaction of 3-Benzoylguaiazulene and Methyl Guaiazulene-3-carboxylate
• The Reaction of Cadalene and Eudalene with Sulfur

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