Synlett 2021; 32(02): 185-191
DOI: 10.1055/s-0040-1707182
cluster
© Georg Thieme Verlag Stuttgart · New York

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
,
Gallardo-Alfonzo S (553435/295485) acknowledges the support of CONACYT through a graduate scholarship. All authors kindly acknowledge to the CIC-UMSNH for financial support of this work. (CIC-UMSNH, México, grant no 2.19).
Further Information

Publication History

Received: 26 March 2020

Accepted after revision: 08 June 2020

Publication Date:
08 July 2020 (online)


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.

Supporting Information

 
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