Selective Synthesis of Indazoloquinolines via Rh(III)‐Catalyzed Oxidant‐Free or Annulation of 2‐Aryl‐2H‐indazoles with α‐Diazo Carbonyl Compounds

A selective synthesis of 5,6‐disubstituted and 5‐substituted indazolo[2,3‐a]quinolines through a Rh(III)‐catalyzed oxidant‐free annulation of 2‐aryl‐2H‐indazoles with α‐diazo carbonyl compounds is reported. With 2‐aryl‐2H‐indazoles as the substrates, α‐diazo carbonyl compounds could act as a C2 synt...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2020-02, Vol.362 (4), p.913-926
Main Authors: Guo, Shenghai, Sun, Lincong, Li, Xuzhuo, Zhang, Xinying, Fan, Xuesen
Format: Article
Language:English
Subjects:
Aromatic compounds
Carbonyl compounds
Carbonyls
Chemical reactions
Chemical synthesis
Organic chemistry
Organic compounds
Oxidation
Oxidizing agents
Substitutes
Substrates
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Summary:A selective synthesis of 5,6‐disubstituted and 5‐substituted indazolo[2,3‐a]quinolines through a Rh(III)‐catalyzed oxidant‐free annulation of 2‐aryl‐2H‐indazoles with α‐diazo carbonyl compounds is reported. With 2‐aryl‐2H‐indazoles as the substrates, α‐diazo carbonyl compounds could act as a C2 synthon to afford 5,6‐disubstituted indazolo[2,3‐a]quinolines via a Rh(III)‐catalyzed [4+2] annulation. On the other hand, when 2‐aryl‐3‐formyl‐2H‐indazoles were used as the substrates, α‐diazo carbonyl compounds switched to act as a C1 synthon to undergo a more complicated [5+1] annulation process to furnish 5‐substituted indazolo[2,3‐a]quinolines.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201901422