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

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)3599-3602
Number of pages4
JournalOrganic Letters
Volume5
Issue number20
DOIs
Publication statusPublished - 2 Oct 2003

Fingerprint

Phenylurea Compounds
Thiohydantoins
Phenylthiourea
Hydantoins
Microwaves
ureas
Urea
Derivatives
microwaves
Microwave irradiation
synthesis
irradiation
N-phenylurea
benzil

Cite this

Muccioli, Giulio G. ; Wouters, Johan ; Poupaert, Jacques H. ; Norberg, Bernadette ; Poppitz, Wolfgang ; Scriba, Gerhard K E ; Lambert, Didier M. / Versatile access to benzhydryl-phenylureas through an unexpected rearrangement during microwave-enhanced synthesis of hydantoins. In: Organic Letters. 2003 ; Vol. 5, No. 20. pp. 3599-3602.
@article{c118af94ecb94783b3ee02819586a0d0,
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 = "10",
day = "2",
doi = "10.1021/ol035282x",
language = "English",
volume = "5",
pages = "3599--3602",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "20",

}

Versatile access to benzhydryl-phenylureas through an unexpected rearrangement during microwave-enhanced synthesis of hydantoins. / Muccioli, Giulio G.; Wouters, Johan; Poupaert, Jacques H.; Norberg, Bernadette; Poppitz, Wolfgang; Scriba, Gerhard K E; Lambert, Didier M.

In: Organic Letters, Vol. 5, No. 20, 02.10.2003, p. 3599-3602.

Research output: Contribution to journalArticle

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=0142011140&partnerID=8YFLogxK

U2 - 10.1021/ol035282x

DO - 10.1021/ol035282x

M3 - Article

VL - 5

SP - 3599

EP - 3602

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 20

ER -