1. Synthesis of 3-aminooxindoles via acid-promoted cyclization of α-imino-N-arylamides and α-azido-N-arylamides.
- Author
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Li, Dianjun, Ma, Haichao, and Yu, Wei
- Subjects
- *
INDOLE compounds , *RING formation (Chemistry) , *CHEMICAL synthesis , *AMIDES , *CHEMICAL sample preparation - Abstract
This paper reports a new method for the synthesis of 3-aminooxindole derivatives. Ethyl 2-( N -arylcarbamoyl)-2-iminoacetates, which can be prepared from the reaction of α-ethoxycarbonyl-α-bromo- N -phenylacetamides with sodium azide, were found to undergo Friedel–Crafts cyclization to afford 3-aminooxindoles in high yield by the catalysis of an acid such as BF 3 ⋅OEt 2 . α-Aryl-α-azido- N -arylamides, on the other hand, were transformed to 3-arylaminooxindoles via a tandem 1,2-aryl migration-dinitrogenation and cyclization by the action of triflic acid. As both ethyl 2-( N -arylcarbamoyl)-2-iminoacetates and α-aryl-α-azido- N -arylamides are easily accessible, the current reactions are expected to be practically useful in the synthesis of 3-aminooxindole derivatives. [ABSTRACT FROM AUTHOR]
- Published
- 2016
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