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Leveraging Pyrazolium Ylide Reactivity to Access Indolizine and 1,2-Dihydropyrimidine Derivatives.
Tran, Ricky; Brownsey, Duncan K; O'Sullivan, Leonie; Brandow, Connor M J; Chang, Emily S; Zhou, Wen; Patel, Ketul V; Gorobets, Evgueni; Derksen, Darren J.
Afiliación
  • Tran R; Faculty of Science, University of Calgary, 2500 University Drive NW, Calgary AB, Canada.
  • Brownsey DK; Faculty of Science, University of Calgary, 2500 University Drive NW, Calgary AB, Canada.
  • O'Sullivan L; Faculty of Science, University of Calgary, 2500 University Drive NW, Calgary AB, Canada.
  • Brandow CMJ; Faculty of Science, University of Calgary, 2500 University Drive NW, Calgary AB, Canada.
  • Chang ES; Faculty of Science, University of Calgary, 2500 University Drive NW, Calgary AB, Canada.
  • Zhou W; Faculty of Science, University of Calgary, 2500 University Drive NW, Calgary AB, Canada.
  • Patel KV; Faculty of Science, University of Calgary, 2500 University Drive NW, Calgary AB, Canada.
  • Gorobets E; Faculty of Science, University of Calgary, 2500 University Drive NW, Calgary AB, Canada.
  • Derksen DJ; Faculty of Science, University of Calgary, 2500 University Drive NW, Calgary AB, Canada.
Chemistry ; 30(28): e202400421, 2024 May 17.
Article en En | MEDLINE | ID: mdl-38478466
ABSTRACT
N-Heterocyclic ylides are important synthetic precursors to rapidly build molecular complexity. Pyrazolium ylides have largely been unexplored, and we demonstrate their diverse utility in this report. We show that these readily accessible building blocks can be used to construct different heterocyclic skeletons by varying the coupling partner. Indolizines can be formed via an N-deletion type mechanism when reacting pyrazolium salts with electron deficient alkynes. 1,2-Dihydropyrimidines can be formed via a rearrangement mechanism when reacting pyrazolium ylides with isocyanates. These reactions enable access to valuable heteroarenes without the need for transition metal catalysis, high temperatures, or strong bases.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Canadá Pais de publicación: Alemania
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: Chemistry Asunto de la revista: QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Canadá Pais de publicación: Alemania