Lateral lithiation and substitution of N'-(2-methylphenyl)- N,N-dimethylurea

Keith Smith; Gamal A. El-Hiti; Sadiq A. Al-Mansury; Mohammed B. Alshammari; Asim A. Balakit

doi:10.3998/ark.5550190.p008.800

Lateral lithiation and substitution of N'-(2-methylphenyl)- N,N-dimethylurea

Keith Smith, Gamal A. El-Hiti, Sadiq A. Al-Mansury, Mohammed B. Alshammari, Asim A. Balakit

Chemistry

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

Lithiation of N'-(2-methylphenyl)-N,N-dimethylurea with three molar equivalents of tert-butyllithium at -40 to -30 °C takes place on the nitrogen and on the methyl group at position 2 of the phenyl group. The lithium intermediate thus obtained reacts with a variety of electrophiles to give the corresponding side-chain substituted derivatives in high yields.

Original language	English
Pages (from-to)	365-375
Number of pages	11
Journal	Arkivoc
Volume	2014
Issue number	5
DOIs	https://doi.org/10.3998/ark.5550190.p008.800
State	Published - 17 Sep 2014

Keywords

Lateral lithiation
Lithium intermediate
N'-(2-methylphenyl)-N
N-dimethylurea

Access to Document

10.3998/ark.5550190.p008.800

Cite this

@article{7f638e3558004743b71a8befcc34b719,

title = "Lateral lithiation and substitution of N'-(2-methylphenyl)- N,N-dimethylurea",

abstract = "Lithiation of N'-(2-methylphenyl)-N,N-dimethylurea with three molar equivalents of tert-butyllithium at -40 to -30 °C takes place on the nitrogen and on the methyl group at position 2 of the phenyl group. The lithium intermediate thus obtained reacts with a variety of electrophiles to give the corresponding side-chain substituted derivatives in high yields.",

keywords = "Lateral lithiation, Lithium intermediate, N'-(2-methylphenyl)-N, N-dimethylurea",

author = "Keith Smith and El-Hiti, \{Gamal A.\} and Al-Mansury, \{Sadiq A.\} and Alshammari, \{Mohammed B.\} and Balakit, \{Asim A.\}",

note = "Publisher Copyright: {\textcopyright} ARKAT-USA, Inc.",

year = "2014",

month = sep,

day = "17",

doi = "10.3998/ark.5550190.p008.800",

language = "English",

volume = "2014",

pages = "365--375",

journal = "Arkivoc",

issn = "1551-7012",

publisher = "Arkat",

number = "5",

}

TY - JOUR

T1 - Lateral lithiation and substitution of N'-(2-methylphenyl)- N,N-dimethylurea

AU - Smith, Keith

AU - El-Hiti, Gamal A.

AU - Al-Mansury, Sadiq A.

AU - Alshammari, Mohammed B.

AU - Balakit, Asim A.

N1 - Publisher Copyright: © ARKAT-USA, Inc.

PY - 2014/9/17

Y1 - 2014/9/17

N2 - Lithiation of N'-(2-methylphenyl)-N,N-dimethylurea with three molar equivalents of tert-butyllithium at -40 to -30 °C takes place on the nitrogen and on the methyl group at position 2 of the phenyl group. The lithium intermediate thus obtained reacts with a variety of electrophiles to give the corresponding side-chain substituted derivatives in high yields.

AB - Lithiation of N'-(2-methylphenyl)-N,N-dimethylurea with three molar equivalents of tert-butyllithium at -40 to -30 °C takes place on the nitrogen and on the methyl group at position 2 of the phenyl group. The lithium intermediate thus obtained reacts with a variety of electrophiles to give the corresponding side-chain substituted derivatives in high yields.

KW - Lateral lithiation

KW - Lithium intermediate

KW - N'-(2-methylphenyl)-N

KW - N-dimethylurea

UR - http://www.scopus.com/inward/record.url?scp=84907184688&partnerID=8YFLogxK

U2 - 10.3998/ark.5550190.p008.800

DO - 10.3998/ark.5550190.p008.800

M3 - Article

AN - SCOPUS:84907184688

SN - 1551-7012

VL - 2014

SP - 365

EP - 375

JO - Arkivoc

JF - Arkivoc

IS - 5

ER -

Lateral lithiation and substitution of N'-(2-methylphenyl)- N,N-dimethylurea

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this