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Synthesis 1995; 1995(3): 321-324
DOI: 10.1055/s-1995-3896
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Metalation of Aryl Iodides, Part II: Directed Ortho-Lithiation of 3-Iodo-N,N-diiospropyl-2-pyridinecarboxamide: Halogen-Dance and Synthesis of an Acyclic Analogue of Meridine

Corinne Cochennec, Patrick Rocca, Francis Marsais, Alain Godard, Guy Quéguiner*
  • *Laboratoire de Chimie Organique Fine de l’IRCOF associé au CNRS, INSA de Rouen, BP 08, F-76131 Mont-Saint-Aignan cédex, France, Fax +33(35)528484; E-mail guy.queguiner@Insa-rouen.fr
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Publication Date:
31 December 2000 (online)

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For the second time, metalation of an iodopyridine was successfully achieved. Lithiation was ortho-directed by the iodo group which subsequently ortho-migrates to give a more stabilized iodolithiopyridine. An intermediate 4-lithio derivative could be trapped with chlorotrimethylsilane before iodo migration had occurred. The final 3-lithio compound was obtained in high yield which was reacted with electrophiles leading to various polysubstituted pyridines. The reaction was used for the preparation of an acyclic analogue of meridine, a new marine alkaloid.

alkaloid - cross coupling - halogen dance - iodopyridine - metalation