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Issue 5, 2013
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Chemodivergent, multicomponent domino reactions in aqueous media: L-proline-catalyzed assembly of densely functionalized 4H-pyrano[2,3-c]pyrazoles and bispyrazolyl propanoates from simple, acyclic starting materials

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Abstract

A library of 4H-pyrano[2,3-c]pyrazol-6-amines was synthesized in excellent yield employing an L-proline-catalyzed, on-water four-component domino reaction from hydrazines, β-dicarbonyl compounds, nitriles and dialkyl acetylenedicarboxylates that generates two rings by the creation of C–C (two), C–N, C[double bond, length as m-dash]N and C–O bonds and presumably involves a sequence of hydrazone formation, cyclocondensation, Michael, [1,3]-hydrogen shift, Michael addition and 6-exo-dig annulation steps. When alkyl propiolates were employed, a three-component reaction took place furnishing alkyl 3,3-bis(5-hydroxy-1H-pyrazol-4-yl)propanoates via a double Michael domino process.

Graphical abstract: Chemodivergent, multicomponent domino reactions in aqueous media: l-proline-catalyzed assembly of densely functionalized 4H-pyrano[2,3-c]pyrazoles and bispyrazolyl propanoates from simple, acyclic starting materials

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Publication details

The article was received on 28 Dec 2012, accepted on 25 Feb 2013 and first published on 25 Feb 2013


Article type: Paper
DOI: 10.1039/C3GC37128J
Citation: Green Chem., 2013,15, 1292-1299
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    Chemodivergent, multicomponent domino reactions in aqueous media: L-proline-catalyzed assembly of densely functionalized 4H-pyrano[2,3-c]pyrazoles and bispyrazolyl propanoates from simple, acyclic starting materials

    P. Prasanna, S. Perumal and J. C. Menéndez, Green Chem., 2013, 15, 1292
    DOI: 10.1039/C3GC37128J

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