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Issue 22, 2011
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Cascade cyclization, dipolar cycloaddition of azomethine imines 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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Publication details

The article was received on 08 Jul 2011, accepted on 17 Aug 2011 and first published on 05 Oct 2011


Article type: Paper
DOI: 10.1039/C1OB06122D
Citation: Org. Biomol. Chem., 2011,9, 7921-7928
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    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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