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Synthesis 2024; 56(02): 267-274
DOI: 10.1055/s-0042-1751504
DOI: 10.1055/s-0042-1751504
paper
Convenient Synthesis of Functionalized Tetracyclic Dihydrochromeno[2,3-b]pyrrolo[3,4-e]pyridine-triones via Four-Component Reactions
We are grateful to the Research Council of Tarbiat Modares University for support of this work.
Abstract
In this research, a simple and efficient strategy for the straightforward synthesis of tetracyclic dihydrochromeno[2,3-b]pyrrolo[3,4-e]pyridine-trione derivatives is presented by a sequential four-component reaction of arylamines, dimethyl acetylenedicarboxylate, alkylamines, and 3-formylchromones as readily available starting materials in MeOH at room temperature. The merit of this sequential enamine formation/1,2-nucleophilic addition/intramolecular aza-Michael addition is highlighted by its high energy conserving (short reaction times at room temperature), excellent yields, metal-free catalyst, easy purification (the products can be purified by simple filtration and washing with EtOH), and green and mild conditions in a one-pot reaction. Presumably, there are no previous reports for the synthesis of these classes of heterocyclic dihydrochromeno[2,3-b]pyrrolo[3,4-e]pyridine-trione derivatives.
Key words
arylamine - dimethyl acetylenedicarboxylate - alkylamine - α-aminomaleimides - formylchromones - multicomponent reactionsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751504.
- Supporting Information
Publication History
Received: 13 June 2023
Accepted after revision: 05 September 2023
Article published online:
02 November 2023
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