A Convenient Synthesis of 1-Aryl- and 2-Aryl-Substituted Indazolones via Intramolecular C-N Coupling Promoted by KOt-Bu

A new method for the synthesis of 1-arylindazolones and 2-arylindazolones from N'-aryl-2-halobenzohydrazides promoted by KOt-Bu was developed. The difference of 2-halogen substituent exerted a significant effect on the distribution of the products. Two distinct reaction pathways are proposed fo...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 48; no. 20; pp. 3551 - 3558
Main Authors Wang, Wei-juan, Chen, Jia-hua, Chen, Zi-cong, Zeng, Yu-feng, Zhang, Xue-jing, Yan, Ming, Chan, Albert S. C.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 17.10.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
potassium tert-butoxide
SERIES
indazolone
radical reaction
RECEPTOR
2-halobenzohydrazide
CATALYST
MURINE
1-ARYL-1H-INDAZOLES
AMINATION
C-N coupling
BIOLOGICAL EVALUATION
SELECTIVITY
KETOHEXOKINASE INHIBITORS
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Summary:A new method for the synthesis of 1-arylindazolones and 2-arylindazolones from N'-aryl-2-halobenzohydrazides promoted by KOt-Bu was developed. The difference of 2-halogen substituent exerted a significant effect on the distribution of the products. Two distinct reaction pathways are proposed for the generation of 1-arylindazolones and 2-arylindazolones, respectively.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0035-1562430