A Two-Step Synthesis of a Novel 7,8-Dihydro-5,8-ethanoindolizine-6,9(5H)-dione

Salvador Gallardo-Alfonzo; Carlos Jesus Cortés-Garcia; Itzel Mejía-Farfán; Yliana López; Martha Mojica; Claudia Contreras-Celedón; Luis Chacón-García

doi:10.1055/s-0040-1707182

Synlett, Table of Contents

Synlett 2021; 32(02): 185-191
DOI: 10.1055/s-0040-1707182

cluster

A Two-Step Synthesis of a Novel 7,8-Dihydro-5,8-ethanoindolizine-6,9(5H)-dione

Salvador Gallardo-Alfonzo

,

Carlos Jesus Cortés-Garcia

,

Itzel Mejía-Farfán

,

Yliana López

,

Martha Mojica

,

Claudia Contreras-Celedón

,

Luis Chacón-García ∗

Abstract

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Published as part of the Cluster Modern Heterocycle Synthesis and Functionalization

Abstract

A two-step synthesis of the novel 5,8-dimethyl-7,8-dihydro-5,8-ethanoindolizine-6,9(5H)-dione from 2,3-dimethyl-1,4-benzoquinone is described. The key step of the synthesis of this unusual fused tricyclic system is the intramolecular regiospecific aza-Michael addition of a pyrrole to an activated double bond by reaction with tetrabutylammonium fluoride under mechanochemical conditions.

Key words

mechanochemistry - quinones - pyrroles - ethanoindolizinediones - organocatalysis

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References

References and Notes
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