Synthesis of Conjugates of 9-(Hydroxymethyl)Methylcytisine with 1,2,3-Triazoles

Abstract

1,3-Dipolar cycloaddition of benzyl azides to the propargyl ether of the 9-hydroxymethyl derivative of the quinolizidine alkaloid methylcytisine under CuAAC conditions synthesized 9-conjugates of it with 1-benzyl-, 1-(4-methoxybenzyl)-, 1-(2,3-dimethoxybenzyl)-, 1-(3,4-dimethoxybenzyl)-, 1-(2-fluorobenzyl)-, 1-(2-chlorobenzyl)-, 1-(4-bromobenzyl)-, 1-(2,4-dichlorobenzyl)-, and 1-(3-nitrobenzyl)-substituted 1,2,3-triazoles. The structures of the synthesized compounds were confirmed by physicochemical analysis, including elemental analysis and NMR spectroscopy.