Organic Letters 2003-10-02

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

Giulio G Muccioli, Johan Wouters, Jacques H Poupaert, Bernadette Norberg, Wolfgang Poppitz, Gerhard K E Scriba, Didier M Lambert

Index: Org. Lett. 5(20) , 3599-602, (2003)

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Abstract

[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.