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Issue 7, 2011
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An straightforward entry to new pyrazolo-fused dibenzo[1,4]diazepines

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Abstract

A series of novel pyrazolodibenzo[1,4]diazepines has been synthesized with good overall yields. The diarylpyrazole intermediates, with structure similarity to biologically relevant compounds such as currently marketed drugs like rimonabant or celecoxib, were prepared by a tandem sequence amine-exchange/heterocyclization starting from readily available enaminones and arylhydrazines. The key step of this efficient methodology was Caryl–N bond construction, accomplished by a palladium-catalyzed intramolecular N-arylation reaction, which was conducted in both homogeneous and polymer-supported versions. Reaction scope of such protocols and recycling of the heterogeneous catalyst were also examined.

Graphical abstract: An straightforward entry to new pyrazolo-fused dibenzo[1,4]diazepines

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Publication details

The article was received on 01 Oct 2010, accepted on 22 Dec 2010 and first published on 07 Feb 2011


Article type: Paper
DOI: 10.1039/C0OB00812E
Citation: Org. Biomol. Chem., 2011,9, 2251-2257
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    An straightforward entry to new pyrazolo-fused dibenzo[1,4]diazepines

    S. Hernández, I. Moreno, R. SanMartin, M. Teresa Herrero and E. Domínguez, Org. Biomol. Chem., 2011, 9, 2251
    DOI: 10.1039/C0OB00812E

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