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Synthesis 2021; 53(21): 4059-4067
DOI: 10.1055/s-0040-1706049
DOI: 10.1055/s-0040-1706049
paper
Molecular Iodine-Mediated Synthesis of 2-Azaanthraquinones from [3.3.3]Propellanes via a Metal-Free Rearrangement
Authors
Financial support of this research from Tarbiat Modares University, Iran, is gratefully acknowledged.
Abstract
A novel iodine-mediated rearrangement of heterocyclic [3.3.3]propellanes under green conditions is described. This metal-free transformation for the straightforward synthesis of substituted 2-azaanthraquinones proceeds via ring opening/dissociation of C–O and C–N bonds/intramolecular C(sp3)–C(sp3) bond formation/ring expansion/aza-ring closure/1,3-N to N alkyl migration. High atom-efficiency, synthetically useful yields, easily accessible starting materials, and mild reaction conditions are advantages of this process.
Keywords
heterocyclic [3.3.3]propellanes - metal-free transformation - redox-mediated rearrangement - amidine rearrangement - 2-azaanthraquinones - one-pot four-component reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706049.
- Supporting Information (PDF)
Publikationsverlauf
Eingereicht: 27. August 2020
Angenommen nach Revision: 31. Mai 2021
Artikel online veröffentlicht:
21. Juli 2021
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