Abstract

HERNANDEZ-MOLINA, Yennys; VERNIEST, Guido; CASALS-HUNG, Magaly  and  ACEVEDO-MARTINEZ, Jorge. Reductive amination of 4,5-dimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde derived from aloe-emodin. Rev Cub Quim [online]. 2019, vol.31, n.3, pp.371-387. ISSN 2224-5421.

The reductive amination of the 1,8-O-protected aloe-emodin carbaldehyde to obtain amino derivatives using different reducing agents and conditions is reported in this article. Aldehyde was obtained in good yield using manganese dioxide as oxidizing agent. The synthesis of two new imines derived from 1,8-O-dimethyl aloe-emodin carbaldehyde is reported as wellin good yields. Sodium borohydride in methanolgave the best conversions as reducing agent for the reductive amination and the conditions were adjusted to increase the conversion to 59 % of the desired product. Same results were obtained starting from the aldehyde or from the imine, in a stepwise or an indirect reductive amination respectively.

Keywords : aloe-emodin; reductive amination; imine; amine; sodium borohydride.

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