Reactions of nitrilium salts with indole and pyrrole and their derivatives in the synthesis of imines, ketones and secondary amines

Robert G. Giles, Harry Heaney, M. John Plater

Research output: Contribution to journalArticle

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Abstract

Reactions of N-methyl- and N-ethyl-nitrilium salts with indole and pyrrole and their derivatives yield imines or imine salts in good yields. The related imines are obtained from the salts after careful basi- fication and hydrolysis of the imine salts or the imines by heating with aqueous base give the related ketones in good yields. Alternatively, the imine salts can be reduced using sodium borohydride in methanol to give the related secondary amines.
Original languageEnglish
Pages (from-to)7367-7385
Number of pages19
JournalTetrahedron
Volume71
Issue number39
Early online date9 May 2015
DOIs
Publication statusPublished - 30 Sep 2015

Keywords

  • Indole(s)
  • Pyrrole(s)
  • Ketones
  • Secondary amines

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