Generation of oxindole-2-thiones (thiols) via dilithiated N-tert-Boc-anilines. Synthesis of a sulfur analog of MK886

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.