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

この論文にアクセスする

この論文をさがす

著者

抄録

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.

収録刊行物

  • 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

参考文献:  6件中 1-6件 を表示

  • <no title>

    SUNDBERG R. J.

    Comprehensive Heterocyclic Chemistry 4, 313-376, 1984

    被引用文献2件

  • <no title>

    SUNDBERG R. J.

    Progress in Heterocyclic Chemistry, 1-5, 1993

    被引用文献1件

  • <no title>

    MATAKA S.

    J. Chem. Soc., Chem. Commun. 1993, 671

    被引用文献1件

  • <no title>

    TSUGE O.

    J. Chem. Soc., Chem. Commun. 60, 4079, 1987

    被引用文献1件

  • <no title>

    JUNEK H.

    Tetrahedron Lett. 1968, 430

    被引用文献1件

  • <no title>

    DANISHEFSKY S.

    J. Org. Chem. 39, 2924, 1974

    被引用文献1件

各種コード

  • NII論文ID(NAID)
    10008891948
  • NII書誌ID(NCID)
    AA00580132
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    00092673
  • データ提供元
    CJP書誌  J-STAGE 
ページトップへ