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NIS Mediated Cross-Coupling of C(sp2)-H and N-H Bonds: A Transition-Metal-Free Approach toward Indolo[1,2-a]quinazolinones
Sindhura Badigenchala,
Published in American Chemical Society
2017
PMID: 28682077
Volume: 82
   
Issue: 14
Pages: 7657 - 7665
Abstract
A metal- and base-free protocol for intramolecular cross-coupling of C(sp2)-H and N-H bonds using N-iodosuccinimide (NIS) has been demonstrated. This environmentally benign approach furnishes a series of substituted indolo[1,2-a]quinazolinones from the suitably fabricated indoles via C-N bond forming cyclization in 28-82% yield. A plausible mechanism is proposed for this cyclization based on the results of a control experiment. This methodology requires no additional metal catalyst, oxidant, or base. Furthermore, the synthetic utility of the protocol is demonstrated by performing a gram scale reaction. © 2017 American Chemical Society.
About the journal
JournalData powered by TypesetJournal of Organic Chemistry
PublisherData powered by TypesetAmerican Chemical Society
ISSN00223263
Open AccessNo
Concepts (26)
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    CATALYSTS
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    Chemical reactions
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    Reaction kinetics
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    Control experiments
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    Cross-couplings
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    Environmentally benign
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    Metal catalyst
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    N-IODOSUCCINIMIDE
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    Plausible mechanisms
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    Quinazolinones
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    SYNTHETIC UTILITY
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    Cyclization
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    Carbon
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    Hydrogen
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    Indole derivative
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    INDOLO[1,2 A]QUINAZOLINONE DERIVATIVE
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    N IODOSUCCINIMIDE
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    Nitrogen
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    Quinazolinone derivative
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    Succinimide derivative
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    Transition element
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    Unclassified drug
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    Article
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    Chemical bond
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    Cross coupling reaction
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    Reaction analysis