Gold‐Catalyzed Carbocyclization/C=N Bond Formation Cascade of Alkyne‐Tethered Diazo Compounds with Benzo[c]isoxazoles for the Assembly of 4‐Iminonaphthalenones and Indenes

A gold‐catalyzed carbocyclization/C=N bond formation cascade reaction has been developed for the synthesis of polyfunctionalized 4‐iminonaphthalenones and indenes in good to high yields under mild reaction conditions. The reaction goes through 5/6‐endo‐dig diazo‐yne carbocyclization to form the endo...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 363; no. 16; pp. 4018 - 4023
Main Authors Bao, Ming, Xie, Xiongda, Hu, Wenhao, Xu, Xinfang
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 13.08.2021
Subjects
4-Iminonaphthalenones
Alkyne Carbocyclization
Benzo[c]isoxazoles
Chemistry
Chemistry, Applied
Chemistry, Organic
Endocyclic Vinyl Carbene
Gold-Catalysis
Physical Sciences
Science & Technology
INSERTION
C-H ANNULATION
4-Iminonaphthalenones
Endocyclic Vinyl Carbene
CARBENE/ALKYNE METATHESIS
Benzo[c]isoxazoles
ENYNONES
Alkyne Carbocyclization
REARRANGEMENT
ALCOHOLS
CYCLOADDITION
EXPEDITIOUS SYNTHESIS
CARBENES
Gold-Catalysis
ANTHRANILS
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Summary:A gold‐catalyzed carbocyclization/C=N bond formation cascade reaction has been developed for the synthesis of polyfunctionalized 4‐iminonaphthalenones and indenes in good to high yields under mild reaction conditions. The reaction goes through 5/6‐endo‐dig diazo‐yne carbocyclization to form the endocyclic vinyl carbene species from corresponding alkyne‐tethered diazo compounds, followed by electrophilic addition/N−O bond cleavage/aromatization sequence with benzo[c]isoxazoles, which features a C=N bond formation process. In addition, the resulting products could be converted into multi‐substituted 2‐naphthol derivatives in high yields.
Bibliography:These authors contributed equally to this work.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202100602