Rh(III)-catalyzed synthesis of 1-aminoindole derivatives from 2-acetyl-1-arylhydrazines and diazo compounds in water

A novel and direct approach to synthesize 1-aminoindole derivatives by Rh(III)-catalyzed cyclization of 2-acetyl-1-arylhydrazines with diazo compounds via aryl C-H activation has been developed. This intermolecular annulation involving tandem C-H activation, cyclization and condensation steps procee...

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Published inChemical communications (Cambridge, England) Vol. 50; no. 46; pp. 6130 - 6133
Main Authors Liang, Yujie, Yu, Ke, Li, Bin, Xu, Shansheng, Song, Haibin, Wang, Baiquan
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2014
Subjects
Activation
Azo Compounds - chemistry
Catalysis
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Condensation
Derivatives
Displays
Hydrazines - chemistry
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Organic chemistry
Organometallic Compounds - chemistry
Oxidants
Physical Sciences
Rhodium - chemistry
Science & Technology
Synthesis
Water - chemistry
FUNCTIONALIZATION
ANNULATION
REGIOSELECTIVE SYNTHESIS
N BOND FORMATION
METHOXYBENZAMIDES
INTERNAL ALKYNES
NONREARRANGED MONOTERPENOID UNIT
CLEAVAGE
C-H ACTIVATION
SIMPLE INDOLE ALKALOIDS
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Summary:A novel and direct approach to synthesize 1-aminoindole derivatives by Rh(III)-catalyzed cyclization of 2-acetyl-1-arylhydrazines with diazo compounds via aryl C-H activation has been developed. This intermolecular annulation involving tandem C-H activation, cyclization and condensation steps proceeds efficiently in water, obviates the need of external oxidants, and displays a broad substituent scope.
Bibliography:ObjectType-Article-1
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ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc01520g