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Article

Ipso- or Cine-Substitutions of 6-Haloimidazo[1,2-a]pyridine Derivatives with Different Azoles Depending on the Reaction Conditions

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Cécile Enguehard,^† Hassan Allouchi,^‡ Alain Gueiffier,*^† and Stephen L. Buchwald^§

EA 3247, Laboratoire de Chimie Thrapeutique, and Laboratoire de Chimie Physique, UFR des Sciences Pharmaceutiques, 31 Avenue Monge, 37200 Tours, France, and Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139

J. Org. Chem., 2003, 68 (14), pp 5614–5617

DOI: 10.1021/jo034439w

Publication Date (Web): June 11, 2003

†

Laboratoire de Chimie Thérapeutique, UFR des Sciences Pharmaceutiques.

‡

Laboratoire de Chimie Physique, UFR des Sciences Pharmaceutiques.

To whom correspondence should be addressed. Fax: +33(0)2 47 36 72 88.

Massachusetts Institute of Technology.

, gueiffier@univ-tours.fr

Abstract

The reactivity of 6-haloimidazo[1,2-a]pyridine toward different azoles is reported. The process was shown to be highly dependent on the reaction conditions. Using copper(I) catalyst, the product of ipso substitution was obtained. In the absence of copper, with cesium carbonate in N,N-dimethylformamide, a cine substitution took place.

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Published In Issue July 11, 2003
Received April 7, 2003

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Article

Ipso- or Cine-Substitutions of 6-Haloimidazo[1,2-a]pyridine Derivatives with Different Azoles Depending on the Reaction Conditions

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

An Extremely Active Catalyst for the Negishi Cross-Coupling Reaction

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N,N-Dimethyl Glycine-Promoted Ullmann Coupling Reaction of Phenols and Aryl Halides

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