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An efficient synthesis of iminoquinones by a chemoselective domino ortho-hydroxylation/oxidation/imidation sequence of 2-aminoaryl ketones
Selvaraj Chandrasekar,
Published in Royal Society of Chemistry
2016
Volume: 14
   
Issue: 11
Pages: 3053 - 3060
Abstract
An efficient chemoselective domino oxidative homocoupling of 2-aminoaryl ketones in the presence of 2-iodoxybenzoic acid (IBX) for the synthesis of iminoquinone has been developed. The domino reaction proceeds via three consecutive steps, such as domino ortho-hydroxylation of 2-aminoaryl ketones, oxidation of a phenol derivative to benzoquinone and dimerization through imine formation to yield iminoquinone. Importantly, this reaction allows the recycling of the oxidant IBX by recovering the by-product iodosobenzoic acid (IBA) and oxidizing it back to IBX. A four step domino strategy for the synthesis of iminoquinone through in situ generation of 2-amino benzophenone from (2-amino phenyl)(phenyl)methanol was also developed. © The Royal Society of Chemistry 2016.
About the journal
JournalData powered by TypesetOrganic and Biomolecular Chemistry
PublisherData powered by TypesetRoyal Society of Chemistry
ISSN14770520
Open AccessNo
Concepts (11)
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    Hydroxylation
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    Reaction kinetics
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    2-IODOXYBENZOIC ACID
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    Chemoselective
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    Domino reactions
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    Efficient synthesis
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    IMINE FORMATION
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    OXIDATIVE HOMOCOUPLING
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    Phenol derivatives
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    SITU GENERATION
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    Ketones