2H-Pyran-2-ones as synthons for (E)-α,β-didehydroamino acid derivatives

Tetrahedron

Volumn 55, Issue 1, 1999, Pages 271-278

  Vraničar, Lidija ^a   Polanc, Slovenko ^a   Kočevar, Marijan ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

Amino acids and derivatives; Isomerisation; NMR; Pyrazoles

Indexed keywords

2 PYRONE DERIVATIVE; AMINO ACID DERIVATIVE; BENZOIC ACID DERIVATIVE; PYRAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0032955958     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01032-1     Document Type: Article

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27. Compound 2 was prepared from benzoylacetone (16.5 g, 0.1 mol) and 4-ethoxymethylene-2-phenyl-5(4H)-oxazolone (21.8 g, 0.1 mol) in methylene chloride (50 mL) in 2 days at room temperature (Method: Behringer, H.; Falkenberg, K. Chem. Ber. 1963, 96, 1428-1435). After evaporation, to the remaining crude product ethanol (200 mL) was added and, upon cooling and filtering off, the resulting product was crystallized from a large amount of ethanol to give pure product 2; mp 154-156 °C, mp lit. 158-160 °C ( Svete, J.; Čadež, Z.; Stanovnik, B.; Tišler, M. Synthesis 1990, 70-72).
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