New Entry for Synthesis of N-Acylhydrazones, Pyridazinones, and 1,3,4-Oxadiazin-6-ones from .ALPHA.-Amino Acid Esters
| Autor: | Masao Wada, Eiko Yasui, Norio Takamura |
|---|---|
| Rok vydání: | 2007 |
| Předmět: |
Magnetic Resonance Spectroscopy
Reducing agent Acylation Hydrazone Stereoisomerism chemistry.chemical_compound Oxazines Drug Discovery Organic chemistry Reactivity (chemistry) Amino Acids chemistry.chemical_classification Hydrazones Esters General Chemistry General Medicine Pyridazines Models Chemical chemistry Electrophile Diazo Tributylphosphine Azo Compounds Oxidation-Reduction |
| Zdroj: | Chemical and Pharmaceutical Bulletin. 55:1652-1654 |
| ISSN: | 1347-5223 0009-2363 |
| DOI: | 10.1248/cpb.55.1652 |
| Popis: | Versatile electrophiles N-acylhydrazones are synthesized via diazotization, reduction, and acylation of alpha-amino acid esters. Reduction of diazo esters with L-selectride 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. |
| Databáze: | OpenAIRE |
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