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Synlett 2011(14): 2029-2034  
DOI: 10.1055/s-0030-1260978
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

An Oxidant-Free Single-Step Synthesis of Tetra- or Disubstituted Symmetrical Pyridine Derivatives by a Hf(OTf)4-Catalyzed Annulation

Toshiaki Sasada, Fuminori Kobayashi, Masato Moriuchi, Norio Sakai, Takeo Konakahara*
Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science (RIKADAI), Noda, Chiba 278-8510, Japan
Fax: +81(4)71239326; e-Mail: konaka@rs.noda.tus.ac.jp;
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Publication History

Received 5 January 2011
Publication Date:
03 August 2011 (online)

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Abstract

The Hf(OTf)4-catalyzed unprecedented annulation of an enamine with triethyl orthoformate leading to the preparation of tetrasubstituted symmetrical pyridine derivatives without an oxidant is described. This method accommodated the single-step synthesis of a disubstituted symmetrical pyridine using an acetophenone derivative, triethyl orthoformate, and ammonium acetate (NH4OAc).

Key words

heterocycles - pyridines - hafnium triflate - enamines - orthoesters

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