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A method for the synthesis of novel fused four‐ring quinoxaline skeleton has been described by an I2 promoted sp3 C−H functionalization between 1,2,3,3‐tetramethyl‐3H‐indolium iodides and 1,2‐diamines. This transformation proceeds smoothly under metal‐ and peroxide‐free conditions through a sequential iodination, oxidation, annulation and rearrangement. Moreover, 8,9‐dichloro‐5,12,12‐trimethyl‐2‐(trifluoromethyl)‐5,12‐dihydroquinolino[2,3‐b]quinoxaline showed good photophysical properties and was used in live cell imaging, indicating the potential value of this skeleton as a fluorophore in probes.

Probe NTR-NO2 was effectively reduced in the presence of NTR generating a highly fluorescent product.

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