Volume 31, Issue 23
Heterocyclic Compounds
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ChemInform Abstract: Synthetic Studies of the Formation of Oxazoles and Isoxazoles from N-Acetoacetyl Derivatives: Scope and Limitations.

Mark Lautens

Mark Lautens

Dep. Chem., Univ. Toronto, Toronto, Ont. M5S 3H6, Can.

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Amelie Roy

Amelie Roy

Dep. Chem., Univ. Toronto, Toronto, Ont. M5S 3H6, Can.

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First published: 08 June 2010

Abstract

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ChemInform Abstract

Treatment of N-acetoacetyl derivatives with NH2OH leads to isoxazoles, whereas reaction with NaN3 generally yields oxazoles. The reactivity of substrates strongly depends on steric and electronic effects. Best results are obtained from substrates containing cyclic amido groups and aliphatic substituents.

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