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Issue 21, 2017
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Regioselective 6-endo-dig iodocyclization: an accessible approach for iodo-benzo[a]phenazines

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Abstract

A facile approach for the synthesis of substituted iodo-benzo[a]phenazines from 2-aryl-3-(aryl/alkylethynyl)quinoxalines via 6-endo-dig ring closure has been described under mild reaction conditions. Iodocyclization proceeds through the iodonium ion intermediate followed by nucleophilic cyclization with the C–H bond of the arene. Furthermore, the resulting 6-iodo-5-aryl/alkyl benzo[a]phenazine derivatives allowed for structural diversification by employing various coupling reactions. The structure of iodo-benzo[a]phenazine was confirmed by X-ray crystallographic studies of the compound.

Graphical abstract: Regioselective 6-endo-dig iodocyclization: an accessible approach for iodo-benzo[a]phenazines

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Publication details

The article was received on 18 Mar 2017, accepted on 04 May 2017 and first published on 05 May 2017


Article type: Paper
DOI: 10.1039/C7OB00671C
Citation: Org. Biomol. Chem., 2017,15, 4686-4696
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    Regioselective 6-endo-dig iodocyclization: an accessible approach for iodo-benzo[a]phenazines

    S. Kumar, M. Mujahid and A. K. Verma, Org. Biomol. Chem., 2017, 15, 4686
    DOI: 10.1039/C7OB00671C

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