Volume 26, Issue 9
Preparative Organic Chemistry
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ChemInform Abstract: 5-Chloropyrazole-4-carbaldehydes as Synthons for Intramolecular 1,3- Dipolar Cycloadditions.

G. L'ABBE

G. L'ABBE

Dep. Chem., Univ. Leuven, B-3001 Leuven, Belg.

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S. EMMERS

S. EMMERS

Dep. Chem., Univ. Leuven, B-3001 Leuven, Belg.

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W. DEHAEN

W. DEHAEN

Dep. Chem., Univ. Leuven, B-3001 Leuven, Belg.

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L. K. DYALL

L. K. DYALL

Dep. Chem., Univ. Leuven, B-3001 Leuven, Belg.

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First published: February 28, 1995

Abstract

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ChemInform Abstract

The title compound (I) is transformed into tricyclic heterocycles (IV), (VI), (IX) or (XI) in a short and attractive reaction sequence consisting of substitution of the chlorine atom, conversion of the aldehyde function into 1,3-dipoles and final intramolecular cycloaddition. Simultaneous Claisen rearrangement of the 5-allyloxy analogue of (III) limits its use for intramolecular 1,3-dipolar cycloaddition. Instead the homologous derivative (XII) can be used.

chemical structure image

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