Highly Diastereoselective Synthesis of 1‑Carbamoyl-4-aminoindoloazepinone Derivatives via the Ugi Reaction

Highly Diastereoselective Synthesis of 1‑Carbamoyl-4-aminoindoloazepinone Derivatives via the Ugi Reaction

A one-pot procedure for the highly diastereoselective synthesis of 1-carbamoyl-4-amino-1,2,4,5-tetrahydroindolo[2,3-c]azepin-3-one derivatives is described. Using 2-formyl-L-tryptophan as a bifunctional building block, a catalyst-free Ugi-three-component reaction (Ugi-3CR) was developed to present t...

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Veröffentlicht in:Organic letters 2013-11, Vol.15 (22), p.5866-5869
Hauptverfasser: Jida, Mouhamad, Betti, Cecilia, Urbanczyk-Lipkowska, Zofia, Tourwé, Dirk, Ballet, Steven
Format: Artikel
Sprache:eng
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Zusammenfassung:A one-pot procedure for the highly diastereoselective synthesis of 1-carbamoyl-4-amino-1,2,4,5-tetrahydroindolo[2,3-c]azepin-3-one derivatives is described. Using 2-formyl-L-tryptophan as a bifunctional building block, a catalyst-free Ugi-three-component reaction (Ugi-3CR) was developed to present trisubstituted indoloazepinones in good yields and excellent diastereomeric excess.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol402940x