Synthesis of Novel Derivatives of 1-Metoxy-3-methylcarbazole – Murrayafoline A Alkaloid

The paper presents the results of a study on the synthesis of new derivatives of the murrayafoline alkaloid, potential inhibitors of tumor processes, which combine in their structure 2 chromatophores: 2-aminopyrimidine and murrayafoline. Pyrimidine-substituted (chloromethylphenyl)carboxylic acid amides, the key intermediates of the synthesis, were prepared by the acylation of 2-[(arylamino)amino]pyrimidine with 4-(chloromethyl)benzoyl chloride. The subsequent alkylation of 1-methoxy-3-methylcarbazole with pyrimidine-substituted (chloromethyl)phenylcarboxylic acid amides in the presence of sodium methoxide gave novel murrayafoline derivatives in yields of 60–80%. As a result of a side nucleophilic reaction with sodium methoxide, the key intermediates partially converted into methyl esters.