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Issue 22, 2011
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Cascade cyclization, dipolar cycloaddition of azomethineimines for the synthesis of pyrazolidines

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Abstract

A tandem multi-step, one-pot reaction of aldehydes with hydrazines has been used for the preparation of tetrahydropyrazoles and dihydropyrazoles. The chemistry involves condensation then cyclization, followed by inter- or intramolecular dipolar cycloaddition of the resulting azomethine imine intermediates. The intramolecular cycloaddition gives fused tricyclic compounds as single diastereoisomers. The intermolecular cycloaddition was successful with a variety of activated alkene and alkyne dipolarophiles.

Graphical abstract: Cascade cyclization, dipolar cycloaddition of azomethine imines for the synthesis of pyrazolidines

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Article information


Submitted
08 Jul 2011
Accepted
17 Aug 2011
First published
05 Oct 2011

Org. Biomol. Chem., 2011,9, 7921-7928
Article type
Paper

Cascade cyclization, dipolar cycloaddition of azomethine imines for the synthesis of pyrazolidines

H. D. S. Guerrand, H. Adams and I. Coldham, Org. Biomol. Chem., 2011, 9, 7921
DOI: 10.1039/C1OB06122D

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