TITLE:
Simple Reduction of Hydantoins with Sodium Borohydride
AUTHORS:
Jun-Ichi Yamaguchi, Emiko Shibuta, Yoshie Oishi
KEYWORDS:
Hydantoin, Reduction, Imidazolidinone
JOURNAL NAME:
International Journal of Organic Chemistry,
Vol.4 No.5,
December
26,
2014
ABSTRACT: The reduction of various hydantoins with sodium borohydride gave the corresponding 4-hydroxy- 2-imidazolidinones in high yields. In contrast, reduction employing a boron trifluoride etherate-sodium borohydride system generated 2-imidazolidinones. In both reductions, the reactivity of the hydantoin was dependent on its substituents. The Lewis acid-promoted reactions of a 4-hydroxy-2-imidazolidinone with nucleophiles were also investigated.