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Demonstrates efficient synthesis of α-carbolines in low-cost conditions, highlighting alternatives to toxic metals.
A DABCO-mediated aza-Michael reaction of sulfonyliminoindoline 1 with α,β-unsaturated aldehyde 2, carried out in DMF at 150 °C, is accompanied by intramolecular N to C migration of the sulfonyl moiety and subsequent [3 + 3]-cyclization to afford 3-sulfonyl α-carbolines 3a with 56–68% yields. If carried out in MeOH at 110 °C, the reaction exclusively yields the carbolines 3b with 59–91% yields. This method avoids toxic metal catalyst/reagents and uses low-cost and simple substrates.
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Chatterjee et al. (2026) studied this question.
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