Synthesis of Imidazolidin-2-ones and Imidazol-2-ones via Base-Catalyzed Intramolecular Hydroamidation of Propargylic Ureas under Ambient Conditions

Alessandra Casnati, Antonio Perrone, Paolo P. Mazzeo, Alessia Bacchi, Raffaella Mancuso, Bartolo Gabriele, Raimondo Maggi, Giovanni Maestri Elena Motti, András Stirling*, Nicola Della Ca'*

*Research Centre for Natural Sciences, Budapest, Hungary; University of Parma, 43124 Parma, Italy, Email: stirling.andrasttk.mta.hu, nicola.dellacaunipr.it

A. Casnati, A. Perrone, P. P. Mazzeo, A. Bacchi, R. Mancuso, B. Gabriele, R. Maggi, G. M. E. Motti, A. Stirling, N. Della Ca', J. Org. Chem., 2019, 84, 3477-3490.

DOI: 10.1021/acs.joc.9b00064 (free Supporting Information)

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Abstract

The phosphazene base BEMP catalyzes an intramolecular hydroamidation of propargylic ureas to provide imidazolidin-2-ones and imidazol-2-ones with  excellent chemo- and regioselectivities under ambient conditions and short reaction times.

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Key Words

imidazolidin-2-ones, organocatalysis

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ID: J42-Y2019