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

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...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2017, Vol.15 (21), p.4686-4696
Main Authors: Kumar, Sonu, Mujahid, Mohammad, Verma, Akhilesh K
Format: Article
Language:English
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob00671c