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Synlett 2021; 32(02): 185-191
DOI: 10.1055/s-0040-1707182
DOI: 10.1055/s-0040-1707182
cluster
A Two-Step Synthesis of a Novel 7,8-Dihydro-5,8-ethanoindolizine-6,9(5H)-dione
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
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707182.
- Supporting Information
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References and Notes
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5,8-Dimethyl-7,8-dihydro-5,8-ethanoindolizine-6,9(5H)-dione (1)
Dione 9 (20 mg, 0.098 mmol) and TBAF (25 mg, 0.098 mmol) were ground in a mortar for 15 min. The product was extracted with Et2O (8–10 mL) and dried under vacuum to give a light-brown solid; yield: 8.0 mg (40%); mp 105–108 °C; Rf
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