Generation of oxindole-2-thiones (thiols) via dilithiatedN-tert-Boc-anilines. Synthesis of a sulfur analog of MK886
- 1 March 1995
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 73 (3) , 336-342
- https://doi.org/10.1139/v95-045
Abstract
The N,C-dilithiated derivatives of the N-tert-butoxycarbonyl-2-alkylthiomethylanilines 5a–c and the N-tert-butoxycarbonyl-2-alkoxycarbonylmethylanilines 11a, b were converted into the N-tert-butoxycarbonyl-oxindole-2-thiones(thiols) 7a–c and 14a, b, respectively, by sequential reaction with carbon disulfide and methyl iodide. Compound 7b was converted into 10d, the sulfur analog of MK886. Keywords: N-tert-butoxycarbonyl-2-alkylthiomethylanilines, dilithiation, N-tert-butoxycarbonyl-2-alkoxycarbonylmethylanilines, N-tert-butoxycarbonyloxindole-2-thiones.Keywords
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