The reaction of arenesulphonyl azides with 2-alkylthiondoles yields 3,3′-azoindoles; however 1-methyl-2-methylthiondole reacts with p-chlorobenzenesulphonyl azide to form 2-p-chlorophenylsulphonylamino-1-methyl-3-methylthioindole. Indoline-2-thione and its N-methyl derivative react with arenesulphonyl azides to form thiadiazoloindoles and Δ3,3′-bi-indoline-2,2′-dithiones.
A. S. Bailey, J. F. Seager and Z. Rashid, J. Chem. Soc., Perkin Trans. 1, 1974, 2384 DOI: 10.1039/P19740002384
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