New Entry for Synthesis of N-Acylhydrazones, Pyridazinones, and 1, 3, 4-Oxadiazin-6-ones from α-Amino Acid Esters

    • YASUI Eiko
    • Department of Pharmaceutical Science, Musashino University
    • WADA Masao
    • Department of Pharmaceutical Science, Musashino University

Abstract

Versatile electrophiles N-acylhydrazones are synthesized via diazotization, reduction, and acylation of α-amino acid esters. Reduction of diazo esters with L-selectride^[○!R]R or tributylphosphine affords the corresponding hydrazones in good yields. Both reducing agents give anti-hydrazones as the major product although the reactivity of each reductant is slightly different. The resulting hydrazones are acylated to give N-acylhydrazones, which are subjected to further reactions to give 1, 3, 4-oxadiazin-6-ones that serve as useful synthetic intermediates for the Diels-Alder reaction.

Journal

Chemical & pharmaceutical bulletin   [List of Volumes]

Chemical & pharmaceutical bulletin 55(11), 1652-1654, 2007-11-01  [Table of Contents]

The Pharmaceutical Society of Japan

References:  19

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Codes

  • NII Article ID (NAID) :
    110006437270
  • NII NACSIS-CAT ID (NCID) :
    AA00602100
  • Text Lang :
    ENG
  • Article Type :
    NOT
  • ISSN :
    00092363
  • NDL Article ID :
    8965703
  • NDL Source Classification :
    ZS51(科学技術--薬学) // ZP1(科学技術--化学・化学工業)
  • NDL Call No. :
    Z53-D167
  • DOI :
    10.1248/cpb.55.1652
  • Databases :
    CJP  NDL  NII-ELS  J-STAGE