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Facile Access to 1 H ‐Indazoles through Iodobenzene‐Catalyzed C–H Amination under Mild, Transition‐Metal‐Free Conditions
Author(s) -
Kashiwa Mitsuhiro,
Sonoda Motohiro,
Tanimori Shinji
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402488
Subject(s) - chemistry , iodobenzene , amination , indazole , catalysis , transition metal , trifluoroacetic acid , medicinal chemistry , halogen , organic chemistry , alkyl
The transition‐metal‐ and halogen‐free synthesis of N ‐aryl‐substituted 1 H ‐indazole and derivatives was accomplished on the basis of the iodobenzene‐catalyzed intramolecular C–H amination of hydrazones under mild conditions. Reactions of hydrazones derived from ketones and hydrazines with a catalytic amount of iodobenzene in the presence of Oxone as an oxidant in trifluoroacetic acid took place to afford 1 H ‐indazoles in moderate to good yields. A plausible reaction mechanism was described on the basis of the control experiments.