A convenient procedure for the preparation of the novel class of tetracyclic imidazo[2,1-c]pyrazolo[1,5-α][1,4]benzodiazepine-5,8-diones is reported. The protocol uses cheap and easily accessible α-amino acids as chiral-pool starting materials and leads to products in an enantiopure form. An intramolecular palladium-catalyzed amination process to form the imidazole nucleus and an intramolecular 1,3-dipolar cycloaddition reaction to simultaneously achieve the pyrazole and 1,4-diazepine rings are the key steps.

Access to a Novel Class of Tetracyclic 1,4-Benzodiazepin-5-ones Starting from alpha-Aminoacids by Pd-Catalyzed Amination/1,3-Dipolar Cycloaddition as Key Steps

BROGGINI, GIANLUIGI
;
2010-01-01

Abstract

A convenient procedure for the preparation of the novel class of tetracyclic imidazo[2,1-c]pyrazolo[1,5-α][1,4]benzodiazepine-5,8-diones is reported. The protocol uses cheap and easily accessible α-amino acids as chiral-pool starting materials and leads to products in an enantiopure form. An intramolecular palladium-catalyzed amination process to form the imidazole nucleus and an intramolecular 1,3-dipolar cycloaddition reaction to simultaneously achieve the pyrazole and 1,4-diazepine rings are the key steps.
2010
Cycloaddition; Diastereoselectivity; Fused-ring systems; Nitrogen heterocycles; Palladium
Basolo, L.; Beccalli, E. M.; Borsini, E.; Broggini, Gianluigi; Khansaa, M.; Rigamonti, M.
File in questo prodotto:
File Dimensione Formato  
EurJOC - 2010, p. 1694 (93).pdf

non disponibili

Tipologia: Versione Editoriale (PDF)
Licenza: Copyright dell'editore
Dimensione 695.32 kB
Formato Adobe PDF
695.32 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11383/1718699
 Attenzione

L'Ateneo sottopone a validazione solo i file PDF allegati

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 33
  • ???jsp.display-item.citation.isi??? 30
social impact