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

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10.3998/ark.5550190.p008.800

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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.\}",

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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 - https://www.scopus.com/pages/publications/84907184688

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

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