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

The Journal of Organic Chemistry
Alessandra CasnatiNicola Della Ca'

Abstract

The first organo-catalyzed synthesis of imidazolidin-2-ones and imidazol-2-ones via intramolecular hydroamidation of propargylic ureas is reported. The phosphazene base BEMP turned out to be the most active organo-catalyst compared with guanidine and amidine bases. Excellent chemo- and regioselectivities to five-membered cyclic ureas have been achieved under ambient conditions, with a wide substrate scope and exceptionally short reaction times (down to 1 min). A base-mediated isomerization step to an allenamide intermediate is the most feasible reaction pathway to give imidazol-2-ones, as suggested by DFT studies.

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Citations

Aug 26, 2020·Chemistry : a European Journal·Thomas R PuleoJeffrey S Bandar
Jul 2, 2021·Chemical & Pharmaceutical Bulletin·Hideaki MatsuoKen-Ichi Fujita
Sep 28, 2021·Organic & Biomolecular Chemistry·Ryukichi Takagi, Duyen Thi Duong

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