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Silver oxide mediated novel SET oxidative cyclization: Stereoselective synthesis of 3-azabicyclo[: N.1.0]alkanes
Kirana Devarahosahalli Veeranna,
Published in Royal Society of Chemistry
2019
PMID: 31198918
Volume: 55
   
Issue: 53
Pages: 7647 - 7650
Abstract
For the first time, silver oxide catalyzed SET-oxidative cyclization of an α-amidinoester tethered with an alkene, leading to a novel cyclopropane-fused cyclic amidine, has been developed. This efficient method permits easy access to the pharmaceutically important 3-azabicyclo[n.1.0]alkane framework, having a quaternary centre. The generality of SET oxidative cyclization using persulfate as a co-oxidant has been demonstrated with a wide variety of α-amidinoesters in good yields. Unusual chemoselective dialkylation of amidine with Grignard reagent and regioselective opening of the cyclopropane ring using organocopper reagent have also been developed. © 2019 The Royal Society of Chemistry.
About the journal
JournalData powered by TypesetChemical Communications
PublisherData powered by TypesetRoyal Society of Chemistry
ISSN13597345
Open AccessNo
Concepts (19)
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    3 AZABICYCLO[N.1.0]ALKANE DERIVATIVE
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    Alkane derivative
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    Alkene
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    Amidine
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    Cyclopropane
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    Grignard reagent
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    Metal oxide
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    SILVER OXIDE
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    Unclassified drug
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    Article
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    Catalysis
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    Cyclization
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    Drug structure
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    Drug synthesis
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    Electron transport
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    OXIDATIVE CYCLIZATION
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    Regioselectivity
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    SINGLE ELECTRON TRANSFER
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    Stereoselectivity