Side-chain lithiation of 2- and 4-substituted pyridines: Synthesis of more complex substituted pyridines

Smith, Keith, El-Hiti, Gamal A., Fekri, Ahmed and Alshammari, Mohammed ORCID: https://orcid.org/0000-0001-9687-8747 2012. Side-chain lithiation of 2- and 4-substituted pyridines: Synthesis of more complex substituted pyridines. Heterocycles 86 (1) , pp. 391-410. 10.3987/COM-12-S(N)33

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Abstract

Lithiation of pyridines substituted in the 2- and 4-positions by acylaminomethyl groups, namely of the corresponding N-pyridinylmethyl)pivalamides, N'-(pyridinylmethyl)-N,N-dimethylureas and tert-butyl N-pyridinylmethylcarbamates, with two mole equivalents of t-BuLi in anhydrous THF at 78 oC takes place on the nitrogen and on the methylene group of the side-chain. The lithium reagents thus obtained react with a variety of electrophiles to give the corresponding side-chain substituted derivatives in high yields.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	Sendai Institute of Heterocyclic Chemistry
ISSN:	0385-5414
Date of First Compliant Deposit:	30 March 2016
Last Modified:	06 May 2023 00:34
URI:	https://orca.cardiff.ac.uk/id/eprint/42876

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