Tetramic acid derivatives via Ugi-Dieckmann-reaction

Tetrahedron Letters

Volumn 50, Issue 15, 2009, Pages 1705-1707

  Spatz, Julia H ^a,b   Welsch, Sebastian J ^a,b   Duhaut, David Emmanuel ^a   Jäger, Nadine ^a   Boursier, Thomas ^a   Fredrich, Martin ^a   Allmendinger, Lars ^c   Ross, Günther ^a   Kolb, Jürgen ^a   Burdack, Christoph ^a   Umkehrer, Michael ^a  

^a Priaxon AG   (Germany)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^c UNIVERSITY OF MUNICH   (Germany)

Author keywords

Cleavable isocyanide; Dieckmann reaction; Heterocycles; Multi component reaction; Tetramic acid derivatives; Ugi reaction

Indexed keywords

TETRAMIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; COMBINATORIAL CHEMISTRY; CYCLIZATION; DRUG SYNTHESIS; POLYMERIZATION; QUANTUM YIELD; UGI DIECKMANN REACTION;

EID: 60649097584     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.01.124     Document Type: Article

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35. General procedure (GP 2) for the synthesis of tetramic acid derivatives 6a-ae: 0.2 mmol of MCR product 5a-ae was dissolved in 4 mL THF (dry), and 0.24 mmol KOtBu were added under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 1 h. After 1 h of reaction time a maximum of conversion was reached, and the reaction mixture was neutralized with 6 N HCl (pH 6-7). The solvent was removed in vacuo. The resulting crude product was purified by flash chromatography on silica (ethyl acetate/hexane).
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