Molecular Iodine-Mediated Synthesis of 2-Azaanthraquinones from [3.3.3]Propellanes via a Metal-Free Rearrangement

Abdolali Alizadeh; Akram Bagherinejad; Mojtaba Khanpour

doi:10.1055/s-0040-1706049

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(21): 4059-4067
DOI: 10.1055/s-0040-1706049

paper

Molecular Iodine-Mediated Synthesis of 2-Azaanthraquinones from [3.3.3]Propellanes via a Metal-Free Rearrangement

Abdolali Alizadeh∗

^aDepartment of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran

,

Akram Bagherinejad

^aDepartment of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran

,

Mojtaba Khanpour

^bState Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, P. R. of China

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Abstract

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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 reaction

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