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An efficient synthesis of the kynurenamines K1 and K2, the major brain and antioxidant metabolites of melatonin 1 is described. Regioselective lithiation of tert-butyl(4-methoxyphenyl) carbamate and iodination provided the (2-iodoaryl)carbamate which when coupled with N-acetyl-propargylamine underwent a Sonogashira reaction. Simultaneous alkyne hydration and N-formylation produced K2, whereas alkyne hydration only, produced K2.
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Amiet et al. (2002) studied this question.