Perilithiation and the synthesis of 8-substituted-1-naphthamides

Jonathan Clayden*, Christopher S. Frampton, Catherine McCarthy, Neil Westlund

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

50 Citations (Scopus)

Abstract

Attempted perilithiation of 1-naphthamides with their 2-positions blocked leads only to nucleophilic attack on the aromatic ring, but perilithiation of naphthalenes bearing 1-substituents such as -NMe2 or CH2NMe2 allows the synthesis of 8-substituted-1-naphthamldes. The 8- CH2NMe2 substituents can be converted to carbonyl groups by Polonovski reactions; other 8-substituents may be introduced by using naphthalic anhydride as a starting material.

Original languageEnglish
Pages (from-to)14161-14184
Number of pages24
JournalTetrahedron
Volume55
Issue number49
DOIs
Publication statusPublished - 3 Dec 1999

Keywords

  • Amides
  • Lithiation
  • Naphthalenes
  • Polonoski reaction

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