Efficient Synthesis of Isothiocyanates Based on the Tandem Staudinger/aza-Wittig Reactions and Mechanistic Consideration of the Tandem Reactions

• Isoda Takeshi

  Medical Research Laboratories, Wyeth K.K.

• Hayashi Kazuhiko

  Medical Research Laboratories, Wyeth K.K.

• Tamai Satoshi

  Medical Research Laboratories, Wyeth K.K.

• Kumagai Toshio

  Medical Research Laboratories, Wyeth K.K.

• Nagao Yoshimitsu

  Graduate School of Pharmaceutical Sciences, The University of Tokushima

Abstract

The tandem and stepwise Staudinger/aza-Wittig reactions of several azides were examined in detail. The tandem reaction method (Method I) exhibited superior results in the yield of the corresponding isothiocyanates bearing an electron-withdrawing group than the conventional stepwise method (Method II) which involves the sequential treatment of the azides with triphenylphosphine and then carbondisulfide. The mechanistic consideration for both reaction methods was proposed on the basis of the ¹H-NMR analyses.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 54 (11), 1616-1619, 2006

  The Pharmaceutical Society of Japan

Keywords

• isothiocyanate
• Staudinger reaction
• phosphazide
• azaylide
• carbapenem antibiotic
• L-084

Details

• CRID: 1390001204171347840
• NII Article ID: 10018306344
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.54.1616
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 8516752
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I8516752
• Web Site: http://www.jstage.jst.go.jp/article/cpb/54/11/54_11_1616/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed