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Synthetic chemistry study reveals a cascade reaction forming stable isoquinolinium 1,4-zwitterions, enabling efficient, catalyst-free synthesis of bioactive pyrrolo[2,1-a]isoquinolines.
A 1,3‐dipolar [3 + 2] cycloaddition/rearrangement cascade process of α ‐alkynyl trifluoromethyl sulfoxides with isoquinoline N ‐oxides toward oxygen‐based isoquinolinium 1,4‐zwitterions bearing a trifluoromethylsulfinyl group is presented. The reaction is readily scalable, and the resulting 1,4‐zwitterions exhibit good bench stability. Furthermore, these zwitterions serve as versatile intermediates in catalyst‐free [3 + 2] cycloaddition/elimination cascades with conjugated ynones, enabling efficient synthesis of biologically relevant pyrrolo[2,1‐ a ]isoquinolines.
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Cao et al. (2026) studied this question.
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