Synthesis of 3-Ethoxycarbonyl-1,2,3,4,5,10-hexahydroindeno[1,2-<i>d</i>]azepine

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  • Masaru Kimura
    Department of Chemistry, Faculty of Science, Okayama University
  • Shiro Morosawa
    Department of Chemistry, Faculty of Science, Okayama University

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<jats:title>Abstract</jats:title> <jats:p>3-Ethoxycarbonyl-1,2,3,4,5,10-hexahydroindeno[1,2-d]azepine (10b) was synthesized from 1-benzylpiperidin-4-one and 1-benzyl-4-[o-(hydroxymethyl)phenyl]hexahydroazepin-4-ol. Compound 10b is of particular interest as an intermediate for the preparation of the hitherto unknown indeno[1,2-d]azepine. It was found that 1-ethoxycarbonyl-4-[o-(hydroxymethyl)phenyl]hexahydroazepin-4-ol and 1-ethoxycarbonyl-4-[o-(hydroxymethyl)phenyl]piperidin-4-ol (16b) give 1-ethoxycarbonylspiro[azepin-4,1′(3H)-isobenzofuran] and 1-ethoxycarbonylspiro[3H-isobenzofuran-1,4′-piperidine] (17b), respectively. Treatment of 16b with 88% formic acid gave 17b and 2-ethoxycarbonyl-2,3,4,9-tetrahydro-1H-indeno[2,1-c]pyridine.</jats:p>

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