A Yb(OTf)₃‐catalyzed [2 + 2] cycloaddition /retro‐electrocyclization (CA‐RE)/ bicyclization of 1‐(2‐aminoarylaklynyl)‐naphthalen‐2‐ols and 3‐ylideneoxindoles is reported, enabling a direct C=C bond cleavage‐reassembly process to regioselectively synthesize a variety of quinoline‐tethered benzo[5,6]chromeno[2,3‐b]indoles in 31‐84% yields. Exchanging the amino group for the hydroxyl group in the arylalkynyl unit of the naphthalen‐2‐ol substrate resulted in chromenyl chromeno[2,3‐b]indoles via a similar cascade process.
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Liu et al. (2024) studied this question.
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