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Synthesis 2019; 51(15): 2936-2944
DOI: 10.1055/s-0037-1612426
DOI: 10.1055/s-0037-1612426
paper
Intramolecular Diels–Alder and [3+2] Cycloaddition Reactions in the One-Pot Synthesis of Epoxypyrrolo[3,4-g]indazoles
We gratefully thank Tarbiat Modares University for financial support.Further Information
Publication History
Received: 03 February 2019
Accepted after revision: 08 March 2019
Publication Date:
10 April 2019 (online)
Abstract
A one-pot approach for the synthesis of epoxypyrrolo[3,4-g]indazoles is presented. The first step was initiated by a three-component reaction of an isocyanide, a dialkyl acetylenedicarboxylate, and 2-furancarboxylic acid, and led to 1,3-dioxoepoxyisoindole, followed by the addition of hydrazonoyl chloride through a [3+2]-cycloaddition reaction in the second step. The key step in the formation of final compound involves a bicyclization strategy through intramolecular Diels–Alder (IMDA) reaction.
Key words
isocyanide - dialkyl acetylenedicarboxylate - 2-furancarboxylic acid - epoxypyrrolo[3,4-g]indazole - IMDA - [3+2] cycloaddition - oxabicyclo compoundsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1612426.
- Supporting Information
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