Synthesis of chromeno[2,3-c]pyrrol-9(2H)-ones by domino Michael-Claisen-SNAr reactions of amino acid esters with 2-chlorophenylpropynones

Synthesis of chromeno[2,3-c]pyrrol-9(2H)-ones by domino Michael-Claisen-SNAr reactions of amino acid esters with 2-chlorophenylpropynones

The domino reaction of amino acid esters with 2-chlorophenylpropynones, readily available by Sonogashira reactions of 2-chlorobenzoylacetylenes, afforded novel chromeno[2,3-c]pyrrol-9(2H)-ones. The domino reaction involves three steps, i.e. Michael, Claisen and SNAr reactions. Intermediates could be...

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Veröffentlicht in:Tetrahedron 2022-01, Vol.104, p.132608, Article 132608
Hauptverfasser: Nguyen Tien, Tuan Anh, Miliutina, Mariia, Radolko, Jan, Thom, Richard, Dang, Tuan T., Ehlers, Peter, Langer, Peter
Format: Artikel
Sprache:eng
Schlagworte:
Amino acids
Cross-coupling reactions
Domino reactions
Heterocycles
Palladium
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Zusammenfassung:The domino reaction of amino acid esters with 2-chlorophenylpropynones, readily available by Sonogashira reactions of 2-chlorobenzoylacetylenes, afforded novel chromeno[2,3-c]pyrrol-9(2H)-ones. The domino reaction involves three steps, i.e. Michael, Claisen and SNAr reactions. Intermediates could be isolated in some cases which allowed to get some insight in the mechanism. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2021.132608