P(4)O(10)/TfOH mediated domino condensation–cyclization of amines with diacids: a route to indolizidine alkaloids under catalyst- and solvent-free conditions

A domino condensation–cyclization method is developed to synthesize indolizidine alkaloids using a P(4)O(10)/TfOH reagent system without the employment of either a catalyst or solvent. The use of a few aliphatic and aromatic dicarboxylic acids is shown along with various primary amines. This method...

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Detalles Bibliográficos
Autores principales: Mandrekar, Ketan S., Tilve, Santosh G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9200442/
https://www.ncbi.nlm.nih.gov/pubmed/35765320
http://dx.doi.org/10.1039/d2ra02534e
Descripción
Sumario:A domino condensation–cyclization method is developed to synthesize indolizidine alkaloids using a P(4)O(10)/TfOH reagent system without the employment of either a catalyst or solvent. The use of a few aliphatic and aromatic dicarboxylic acids is shown along with various primary amines. This method is suitable for synthesizing pyrrolo[2,1-a]isoquinolines, pyrido[2,1-a]isoquinolines, and isoindolo[1,2-a]isoquinolinones in excellent yields. When phthalic acid is used, a workup with either NaBH(4) or a saturated NaHCO(3) solution provided 12b-H or 12b-OH isoindolo[1,2-a]isoquinolinones, respectively.

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