Access to a Novel Class of Tetracyclic 1,4-Benzodiazepin-5-ones Starting from a-Amino Acids by Pd-Catalyzed Amination/1,3-Dipolar Cycloaddition as the Key Steps
Articolo
Data di Pubblicazione:
2010
Citazione:
Access to a Novel Class of Tetracyclic 1,4-Benzodiazepin-5-ones Starting from a-Amino Acids by Pd-Catalyzed Amination/1,3-Dipolar Cycloaddition as the Key Steps / L. Basolo, E.M. Beccalli, E. Borsini, G. Broggini, M. Khansaa, M. Rigamonti. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2010:9(2010), pp. 1694-1703. [10.1002/ejoc.200901290]
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.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Cycloaddition; Diastereoselectivity; Fused-ring systems; Nitrogen heterocycles; Palladium
Elenco autori:
L. Basolo, E.M. Beccalli, E. Borsini, G. Broggini, M. Khansaa, M. Rigamonti
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