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Naphthalene-catalysed Lithiation of Chlorinated Nitrogenated Aromatic Heterocycles and Reaction with Electrophiles

✍ Scribed by Inmaculada Gómez; Emma Alonso; Diego J Ramón; Miguel Yus

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 173 KB
Volume: 56
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(00)00318-5

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✦ Synopsis

AbstractÐNaphthalene catalysed reductive lithiation of various chloroazines (1, 7,10,13) in the presence of different electrophiles yields, after hydrolysis, the expected functionalised heterocycles with one (2, 8), two (11, 14a±d) and three nitrogen atoms in the ring (14e,f). This methodology allowed us to trap in situ the lithium imine derived from the reaction of 2-pyridyllithium with benzonitrile, by reaction with a Grignard reagent in the presence of titanium alkoxides. 2,4-Dimethoxypyrimidines (14a,c,d) are demethylated under acidic conditions to give the corresponding uracil derivatives 16.

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