Ortho-[(alkylthio)(aminocarbonyl)methyl]anilines
AssigneeThe Ohio State University Research Foundation
InventorPaul G. Gassman
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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-[thioether (hydrocarbonoxycarbonyl) alkyl]aniline, or a [thioether (aminocarbonyl) alkyl]aniline, reacting the orthosubstituted 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.
Claims3
A compound having a formula ##STR8## wherein R is hydrogen, a hydrocarbon radical free from aliphatic unsaturation and containing from 1 to 8 carbon atoms, or a lower alkanoyl;
- R.sup.1 is lower alkyl, phenyl or benzyl;
- R.sup.2 is hydrogen, lower alkyl, phenyl or benzyl;
- each R.sup.4 is hydrogen or a lower alkyl;
- each of Y and Z is hydrogen or a substituent selected from the group consisting of halogen, nitro, cyano, lower alkyl and lower alkyloxy.
Dependencies are inferred from the claim text.