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Issue 45, 2017
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The diaza-Nazarov cyclization involving a 2,3-diaza-pentadienyl cation for the synthesis of polysubstituted pyrazoles

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Abstract

An unprecedented iodine-mediated diaza-Nazarov (DAN) type cyclization for the construction of substituted pyrazoles from easily available starting materials via an enamine–iminium ion intermediate is described. The oxidative cyclization worked under green conditions with remarkable regioselectivity. This one-pot, efficient and operationally simple three-component intramolecular regioselective DAN cyclization displayed a wide range of substrate scope. The dichotomy of reaction pathways has been explored with density functional theory in the gas phase and solution phase. Of the possible 1,5-, 1,6-, and 1,7-electrocyclizations, the DAN cyclization, i.e., the 1,5-pathway offers the lowest activation energy barrier supporting our experimental observations.

Graphical abstract: The diaza-Nazarov cyclization involving a 2,3-diaza-pentadienyl cation for the synthesis of polysubstituted pyrazoles

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Publication details

The article was received on 05 Aug 2017, accepted on 31 Oct 2017 and first published on 08 Nov 2017


Article type: Paper
DOI: 10.1039/C7OB01949A
Citation: Org. Biomol. Chem., 2017,15, 9643-9652
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    The diaza-Nazarov cyclization involving a 2,3-diaza-pentadienyl cation for the synthesis of polysubstituted pyrazoles

    B. Aegurla and R. K. Peddinti, Org. Biomol. Chem., 2017, 15, 9643
    DOI: 10.1039/C7OB01949A

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