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Mapping of Some Further Alkylation-Initiated Pathways to Polyheterocyclic Compounds from Indigo and Indirubin.
Ali, Sarfaraz; McCosker, Patrick M; Willis, Anthony C; Pyne, Stephen G; Richardson, Christopher; Bremner, John B; Keller, Paul A.
Afiliación
  • Ali S; School of Chemistry and Molecular Bioscience, Molecular Horizons, University of Wollongong, Wollongong, NSW 2522, Australia.
  • McCosker PM; School of Chemistry and Molecular Bioscience, Molecular Horizons, University of Wollongong, Wollongong, NSW 2522, Australia.
  • Willis AC; Research School of Chemistry, Australian National University, Canberra, ACT 2601, Australia.
  • Pyne SG; School of Chemistry and Molecular Bioscience, Molecular Horizons, University of Wollongong, Wollongong, NSW 2522, Australia.
  • Richardson C; School of Chemistry and Molecular Bioscience, Molecular Horizons, University of Wollongong, Wollongong, NSW 2522, Australia.
  • Bremner JB; School of Chemistry and Molecular Bioscience, Molecular Horizons, University of Wollongong, Wollongong, NSW 2522, Australia.
  • Keller PA; School of Chemistry and Molecular Bioscience, Molecular Horizons, University of Wollongong, Wollongong, NSW 2522, Australia.
Molecules ; 29(17)2024 Sep 06.
Article en En | MEDLINE | ID: mdl-39275089
ABSTRACT
The reaction of indigo with two equivalents of the electrophile ethyl bromoacetate with caesium carbonate as a base result in the formation of structurally complex polyheterocyclics, including a fused spiroimidazole and a spiro[1,3]oxazino derivative, together with a biindigoid-type derivative, through a convenient one-pot reaction. Further assessment of the reaction using five equivalents of the electrophile gave rise to other molecules incorporating the 2-(7,13,14-trioxo-6,7,13,14-tetrahydropyrazino[1,2-a4,3-a']diindol-6-yl) scaffold. The reaction of ethyl bromoacetate with the less reactive indirubin resulted in the synthesis of three derivatives of a new class of polyheterocyclic system via a cascade process, although yields were low. These compounds were derived from the parent indolo[1,2-b]pyrrolo[4,3,2-de]isoquinoline skeleton. Despite the modest yields of the reactions, they represent quick cascade routes to a variety of heterocycles from cheap starting materials, with these structures otherwise being difficult to synthesise in a traditional stepwise manner. These outcomes also contribute significantly to the detailed understanding of the indigo/indirubin cascade reaction pathways initiated by base-catalysed N-alkylation.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Molecules Asunto de la revista: BIOLOGIA Año: 2024 Tipo del documento: Article País de afiliación: Australia Pais de publicación: Suiza
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Molecules Asunto de la revista: BIOLOGIA Año: 2024 Tipo del documento: Article País de afiliación: Australia Pais de publicación: Suiza