perchloric acid in methanol Michael addition; 0.75 h; Heating;

aluminum oxide in water T=110°C; 12 h; chemospecific reaction;

1: para-nitro iodo-benzene; 3-hydroxy-3-phenyl-prop-1-yne With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine in tetrahydrofuran Sonogashira coupling; 16 h; Heating; 2: 2-amino-benzenethiol With acetic acid; triethylamine in tetrahydrofuran 20 h; Heating;

2.1: piperidine / methanol / 0.5 h / 20 °C 2.2: 20 °C / Reflux View Scheme

2.1: piperidine / methanol / 0.5 h / 20 °C 2.2: 20 °C / Reflux View Scheme

1: sodium hydroxide 2: methanol / |Acidic conditions View Scheme