Tetrahedron

Naphthalene-catalysed lithiation of chlorinated nitrogenated aromatic heterocycles and reaction with electrophiles

I Gómez, E Alonso, DJ Ramón, M Yus

Index: Gomez, Inmaculada; Alonso, Emma; Ramon, Diego J.; Yus, Miguel Tetrahedron, 2000 , vol. 56, # 24 p. 4043 - 4052

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Citation Number: 42

Abstract

Naphthalene 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 ...