Directed ortho??lithiation of chloroquinolines. Application to synthesis of 2, 3??disubstituted quinolines

F Marsais, A Godard…

Index: Marsais, F.; Godard, A.; Queguiner, G. Journal of Heterocyclic Chemistry, 1989 , vol. 26, p. 1589 - 1594

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Citation Number: 48

Abstract

Abstract 2-, 3-and 4-Chloroquinolines were selectively lithiated at low temperature by lithium diisopropylamide at the more acidic C-3, C-4 and C-3 positions respectively. Reaction of 2- chloro-3-lithioquinoline with electrophiles led to various 2, 3-disubsthuted quinolines. The versatility of this functionalization methodology is enhanced by the C-2 halogen reactivity towards oxygen or nitrogen nucleophiles. So, a great variety of 2, 3-di-substituted ...

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