A Novel Degydrative Ring-Transformation of 1-Alkyl-3-aroypyrrolidenes into 1-Alkyl-2-aryl-3-methylpyrroles

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Abstract

When heated in an alcoholic solvent, such as ethylene glycol or butanol, 4-substituted 3-aroyl-1-alkylpyrrolidines, which are readily accessible via the condensation of an amino acid, paraformaldehyde, and 3-substituted 1-ary-2-propen-1-one, afforded 4-substituted 1-alkyl-2-aryl-3-methylpyrrole derivatives in good yields. The ring-transformation of 3,4-dibenzoyl-1-methyl-2-phenylpyrrolidine occurred in two directions, giving the corresponding 3-benzyl- and 3-methylpyrrole derivative. Also, bicyclic pyrroles, such as 1<i>H</i>,3<i>H</i>-pyrrolo[1,2-<i>c</i>]thiazole, 2,3-dihydro-1<i>H</i>-pyrrolizine, and 5,6,7,8-tetrahydroindolizine, were prepared by the ring-transformation of bicyclic aroylpyrrolidines obtained from the corresponding cyclic amino acids. A mechanism for the ring-transformation is proposed.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 68(7), 1969-1979, 1995-07-15

    The Chemical Society of Japan

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Codes

  • NII Article ID (NAID)
    10008891948
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • Data Source
    CJP  J-STAGE 
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