A metal-free synthesis of 2-benzylideneindolin-3-ones via a formal [4+1] annulation reaction from o-azidobenzaldehydes and terminal alkynes has been developed. The method features operational simplicity, mild reaction conditions and ready availability of starting materials. A broad range of 2-benzylideneindolin-3-ones were prepared in moderate to excellent yields. Mechanism studies indicated that the reaction may proceed via a nucleophilic addition/rearrangement/azide-alkene cycloaddition pathway to produce 2-benzylideneindolin-3-ones.
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Tang et al. (2024) studied this question.
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