Synthesis of Dibenzo[d, g][1, 3, 6]trithiocins

Access this Article

Search this Article

Author(s)

Abstract

6-Acetoxy-, 6-methoxy-, 6-azido-, and 6-(methylthio)dibenzo[<i>d</i>,<i>g</i>][1,3,6]trithiocins (<b>13</b>, <b>14</b>, <b>17</b>, and <b>18</b>, respectively) were synthesized by reactions of 9a<i>H</i>-9,10-dithia-4b-thioniaindeno[1,2-<i>a</i>]indene chloride (<b>4</b>) with appropriate nucleophiles in good yields. The trithiocin <b>13</b> was also prepared by the Pummerer reaction of dibenzo[<i>d</i>,<i>g</i>][1,3,6]trithiocin 5-oxide (<b>12</b>) in 97% yield. In many reactions of <b>4</b> with nucleophiles, the trimeric partial hydrolysis product, bis{<i>o</i>-[(dibenzo[<i>d</i>,<i>g</i>][1,3,6]trithiocin-6-yl)thio]phenyl} sulfide (<b>15</b>), was formed either as the major or a minor product. Structure of <b>15</b> was determined by X-ray diffraction analysis. Meanwhile, heating <b>4</b> in boiling methanol or ethanol gave the hydrolysis product, bis(<i>o</i>-mercaptophenyl) sulfide (<b>16</b>), in good yields. Condensation of <b>16</b> with benzaldehyde and pivalaldehyde gave 6-phenyl- and 6-<i>t</i>-butyldibenzo[<i>d</i>,<i>g</i>][1,3,6]trithiocins in good yields.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 71(5), 1187-1192, 1998-05-15

    The Chemical Society of Japan

References:  12

  • <no title>

    NAKAYAMA J.

    J. Chem. Soc., Chem. Commun. 1996, 205

    Cited by (2)

  • <no title>

    NAKAYAMA J.

    Bull. Chem. Soc. Jpn. 69, 2349, 1996

    Cited by (2)

  • <no title>

    GLASS R. S.

    Conformational Analysis of Medium-Sized Heterocycles, 1988

    Cited by (1)

  • <no title>

    Stereochemistry of Heterocyclic Compounds, Part II, 1977

    Cited by (1)

  • <no title>

    Comprehensive Heterocyclic Chemistry II 9, 404-735, 1996

    Cited by (1)

  • <no title>

    BURKE L. P.

    J. Am. Chem. Soc. 119, 8313, 1997

    Cited by (1)

  • <no title>

    BLOCK E.

    J. Am. Chem. Soc. 111, 658, 1989

    Cited by (7)

  • <no title>

    NAKAYAMA J.

    Tetrahedron Lett. 24, 3729, 1983

    Cited by (1)

  • <no title>

    NAKAYAMA J.

    Bull. Chem. Soc. Jpn. 49, 3567, 1976

    Cited by (3)

  • <no title>

    ALTOMARE A.

    J. Appl. Crystallogr. 27, 435, 1994

    Cited by (65)

  • <no title>

    MALLINSON P. R.

    J. Appl. Crystallogr. 28, 31, 1995

    Cited by (1)

  • <no title>

    ELHADI F. E.

    Angew. Chem. 88, 224, 1976

    DOI  Cited by (1)

Codes

  • NII Article ID (NAID)
    10008932073
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • NDL Article ID
    4473878
  • NDL Source Classification
    ZP1(科学技術--化学・化学工業)
  • NDL Call No.
    Z53-B35
  • Data Source
    CJP  NDL  J-STAGE 
Page Top