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Reaction of Hydantoin with Boronic Acids

✍ Scribed by Erin A. Gwynne; Jenna C. Holt; Jerrod R. Dwan; Francis E. Appoh; Christopher M. Vogels; Andreas Decken; Stephen A. Westcott

Publisher
John Wiley and Sons
Year
2010
Tongue
German
Weight
191 KB
Volume
93
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

We have examined the reaction of hydantoin (=imidazolidine‐2,4‐dione) with (formylphenyl)boronic acids, where the addition of a boronic acid group is hoped to increase bioactivities. Addition of (2‐formylphenyl)boronic acid to hydantoin gave an unexpected azaborine compound, which presumably arises by initial formation of the (phenylmethylidene)hydantoin, with subsequent loss of H~2~O to give the cyclized product. Reactions of (3‐formylphenyl)‐ and (4‐formylphenyl)boronic acids with hydantoin gave the corresponding [(Z)‐phenylmethylidene]hydantoins in good‐to‐excellent yields. Attempts to use (3‐formylthiophen‐2‐yl)boronic acid gave a product where the boronic acid group has been cleaved.

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