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

doi:10.1021/ol035282x

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

Unite de recherche en chimie physique, theorique et structurale

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

(Equation presented) 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.

langue originale	Anglais
Pages (de - à)	3599-3602
Nombre de pages	4
journal	Organic Letters
Volume	5
Numéro de publication	20
Les DOIs	https://doi.org/10.1021/ol035282x
Etat de la publication	Publié - 2 oct. 2003

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10.1021/ol035282x

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CCDC 211705: Experimental Crystal Structure Determination
Lambert, D. M. (Contributeur), Muccioli, G. (Contributeur), NORBERG, B. (Contributeur), Poppitz, W. (Contributeur), Poupaert, J. H. (Contributeur), Scriba, G. K. E. (Contributeur) & Wouters, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2004
DOI: 10.5517/cc7396t, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc7396t&sid=DataCite
Ensemble de données

Contient cette citation

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title = "Versatile access to benzhydryl-phenylureas through an unexpected rearrangement during microwave-enhanced synthesis of hydantoins",

abstract = "(Equation presented) 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.",

author = "Muccioli, {Giulio G.} and Johan Wouters and Poupaert, {Jacques H.} and Bernadette Norberg and Wolfgang Poppitz and Scriba, {Gerhard K E} and Lambert, {Didier M.}",

year = "2003",

month = oct,

day = "2",

doi = "10.1021/ol035282x",

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volume = "5",

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journal = "Organic Letters",

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T1 - Versatile access to benzhydryl-phenylureas through an unexpected rearrangement during microwave-enhanced synthesis of hydantoins

AU - Muccioli, Giulio G.

AU - Wouters, Johan

AU - Poupaert, Jacques H.

AU - Norberg, Bernadette

AU - Poppitz, Wolfgang

AU - Scriba, Gerhard K E

AU - Lambert, Didier M.

PY - 2003/10/2

Y1 - 2003/10/2

N2 - (Equation presented) 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.

AB - (Equation presented) 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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U2 - 10.1021/ol035282x

DO - 10.1021/ol035282x

M3 - Article

AN - SCOPUS:0142011140

SN - 1523-7060

VL - 5

SP - 3599

EP - 3602

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

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

Résumé

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Autres fichiers et liens

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Ensembles de données

CCDC 211705: Experimental Crystal Structure Determination

Contient cette citation