Abstract
A novel synthesis of substituted β-carboline-3-esters was achieved by the molecular iodine catalyzed reaction of tryptophan methyl ester hydrochlorides with methyl ketones through oxidative C(CO) − C(methyl) bond cleavage. The products in these reactions are similar to those produced in regular Pictet-Spengler reactions of tryptophan methyl esters with analogous aldehyde substrates. Studies revealed that, reaction involves iminium formation, cyclization and followed by iodine catalyzed C(CO) − C(alkyl) bond cleavage of methyl group of ketone substrate to the final compound.
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