What question did this study set out to answer?

To develop a DABCO-mediated reaction for the synthesis of 2-substituted α-carbolines and their 3-sulfonyl derivatives.

May 16, 2026

DABCO-Mediated Straightforward Syntheses of 2-Substituted α-Carbolines and Their 3-Sulfonyl Derivatives

Puntos clave

To develop a DABCO-mediated reaction for the synthesis of 2-substituted α-carbolines and their 3-sulfonyl derivatives.
Used DABCO to mediate the reaction of sulfonyliminoindoline with α,β-unsaturated aldehyde.
Conducted reactions in DMF at 150 °C and MeOH at 110 °C for different products.
Achieved 56–68% yields of 3-sulfonyl α-carbolines at high temperature in DMF.
Obtained 59–91% yields of carbolines in methanol under milder conditions.
Demonstrated a method avoiding toxic metal catalysts with low-cost substrates.

Resumen

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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Cite This Study

Chatterjee et al. (Thu,) studied this question.

synapsesocial.com/papers/6a0809d7a487c87a6a40ba37 https://doi.org/https://doi.org/10.1021/acs.joc.6c00121

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