Control of Site of Lithiation of 3-(Aminomethyl)pyridine Derivatives

doi:10.1055/S-0033-1338547

Paper

Control of Site of Lithiation of 3-(Aminomethyl)pyridine Derivatives

Published Oct 9, 2013 · Keith Smith, G. El‐Hiti, Mohammed B. Alshammari

Synthesis

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Abstract

Lithiation of N -(pyridin-3-ylmethyl)pivalamide, tert -butyl N -(pyridin-3-ylmethyl)carbamate, and N , N -dimethyl- N ′-(pyridin-3-ylmethyl)urea with tert -butyllithium (3 equiv) in anhydrous tetrahydrofuran at –78 °C takes place on the nitrogen and on the ring at the 4-position. The dilithium reagents thus obtained react with various electrophiles to give the corresponding substituted derivatives in high yields. On the other hand, regioselective side-chain lithiation occurs with lithium diisopropylamide (3.3 equiv) at –20 to 0 °C. A mixture of ring and side-chain substitution products is obtained with n -butyllithium as the lithium reagent. Treatment of one of the ring-substituted products with trifluoroacetic anhydride in dichloromethane under reflux conditions led to formation of the corresponding 1 H -pyrrolo[3,4- c ]pyridine in high yield.

Study Snapshot

Lithiation of 3-(aminomethyl)pyridine derivatives with tert-butyllithium at -78°C leads to high yields of substituted derivatives, while regioselective side-chain lithiation with lithium diisopropylamide at -20 to

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Control of Site of Lithiation of 3-(Aminomethyl)pyridine Derivatives

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References

Citations

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This study successfully synthesized 2-diphenylphosphinomethyl-3-methylpyrazine in 70-85% yield using n-BuLi metalation and Ph2PCl, demonstrating its regioselectivity and environmental friendliness.

Spectroscopic Characterization, Hirshfeld Surface, DFT, and TD-DFT of tert-Butyl Phenethylcarbamate and 1,1-Dimethyl-3-Phenethylurea

Tert-butylphenethylcarbamate and 1,1-dimethyl-3-phenethylurea show good correlation between experimental and predicted spectral data, with the closest interactions between hydrogen atoms.

Convenient Synthesis of New Heterocycles Containing the Quinoxaline Ring System

This study presents a simple and convenient method for synthesizing new heterocycles containing quinoxaline moiety using commercially available chemicals, offering a potential route for difficult-to-synthesise compounds.

Synthesis of novel heterocycles using 1,2,3‐triazole‐4‐carbohydrazides as precursors

This study demonstrates efficient and simple methods for synthesizing novel heterocycles containing 1,2,3-triazole using 1,2,3-triazole-4-carbohydrazides as precursors, offering potential applications in various fields.

Synthesis and Structure Elucidation of N′-(4-Methoxybenzylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide

N′-(4-Methoxybenzylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide (3) is a novel compound with potential applications in pharmaceuticals and nutraceuticals.