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Selective Synthesis of Indazolo[2,3‐ a ]quinolines via Rh(III)‐Catalyzed Oxidant‐Free [4+2] or [5+1] Annulation of 2‐Aryl‐2 H ‐indazoles with α ‐Diazo Carbonyl Compounds
Author(s) -
Guo Shenghai,
Sun Lincong,
Li Xuzhuo,
Zhang Xinying,
Fan Xuesen
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901422
Subject(s) - annulation , chemistry , synthon , diazo , aryl , catalysis , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , alkyl
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‐2 H ‐indazoles with α ‐diazo carbonyl compounds is reported. With 2‐aryl‐2 H ‐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‐2 H ‐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.