Synthesis of oxindoles from anilines and intermediates therein

Details Synthesis of oxindoles from anilines and intermediates therein Synthesis of oxindoles from anilines and intermediates therein

1975-03-31

1976-12-07

Mars, Howard T.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260465R, 260465C, C07C14940

Patent

active

039962644

ABSTRACT:
Preparing oxindoles and intermediates therefor by reacting an N-haloaniline with .beta.-thio esters or .beta.-thio amides to form an azasulfonium halide, reacting the azasulfonium halide with a base to form an ortho-[thio-ether (hydrocarbonoxycarbonyl) alkyl]aniline, or a [thio-ether (aminocarbonyl) alkyl]aniline, reacting the ortho-substituted aniline with an acid to form a 3-thio-ether-2-oxindole, and then reducing the 3-thio-ether-2-oxindole with Raney Nickel to form the 2-oxindole.

REFERENCES:
gassman et al., J. Am. Chem. Soc. 95 pp. 2718-2719, Apr. 18, 1973.

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