Versatile access to benzhydryl-phenylureas through an unexpected rearrangement during microwave-enhanced synthesis of hydantoins.

Muccioli, Giulio;Wouters, Johan;Poupaert, Jacques;Norberg, Bernadette;Lambert, Didier;et.al.
(2003) Organic Letters — Vol. 5, n° 20, p. 3599-3602 (2003)

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[reaction: see text] A new access to benzhydryl-phenylureas is described. These new interesting urea derivatives were obtained by reaction of substituted benzils with substituted phenylureas under microwave irradiation. Phenylthiourea, when reacted with benzil, gave 3-phenyl-thiohydantoin. Moreover, benzylurea, as phenethylurea, gave the corresponding 3-substituted hydantoin derivatives, demonstrating that only phenylurea derivatives can result in benzhydryl-phenylureas under the applied conditions. This new reaction proved to be an easy access to substituted 1-benzhydryl-3-phenyl-ureas.
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Muccioli, G., Wouters, J., Poupaert, J., Norberg, B., Poppitz, W., Scriba, G. K. E., & Lambert, D. (2003). Versatile access to benzhydryl-phenylureas through an unexpected rearrangement during microwave-enhanced synthesis of hydantoins. Organic Letters, 5(20), 3599-3602. https://doi.org/10.1021/ol035282x (Original work published 2003)