El-Hiti, Gamal, Smith, Keith and Alshammari, Mohammed  ORCID: https://orcid.org/0000-0001-9687-8747
2012.
Lithiation and Substitution of N′-(ω-Phenylalkyl)-N,N-dimethylureas.
Synthesis (Stuttgart)
44
(3)
, pp. 2013-2022.
10.1055/s-0031-1291008
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Abstract
Lithiation of N′-phenethyl-N,N-dimethylurea with three equivalents of tert-butyllithium in anhydrous tetrahydrofuran at -78 °C takes place on the nitrogen and on the side-chain of the CH2 next to the phenyl ring (α-lithiation). The 2-lithio isomer can be obtained via bromine-lithium exchange of N′-2-(2-bromophenyl)ethyl-N,N-dimethylurea using methyllithium followed by tert-butyllithium in tetrahydrofuran at -78 °C. The lithium reagents thus obtained react with various electrophiles to give the corresponding substituted derivatives in excellent yields. Lithiation of N′-(3-phenylpropyl)-N,N-dimethylurea takes place on the α-CH2 with tert-butyllithium at 0 °C. On the other hand, lithiation of N′-(4-phenylbutyl)-N,N-dimethylurea with tert-butyllithium at 0 °C takes place on one of the methyl groups of the urea unit.
| Item Type: | Article |
|---|---|
| Date Type: | Publication |
| Status: | Published |
| Schools: | Schools > Chemistry |
| Subjects: | Q Science > QD Chemistry |
| Uncontrolled Keywords: | N′-phenethyl-N,N-dimethylurea - side-chain lithiation - bromine-lithium exchange - electrophile - synthesis |
| Publisher: | Georg Thieme Verlag |
| ISSN: | 0039-7881 |
| Date of First Compliant Deposit: | 30 March 2016 |
| Last Modified: | 10 May 2023 17:51 |
| URI: | https://orca.cardiff.ac.uk/id/eprint/35737 |
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