Abstract

AbstractMultifunctionalized 1,2,4‐triazolidines have been synthesized by a ruthenium porphyrin‐catalyzed three‐component coupling reaction. In a one‐pot reaction, ruthenium porphyrins catalyzed the in situ generation of azomethine ylides from α‐diazo esters and imines. Stereoselective 1,3‐dipolar cycloaddition reactions of the azomethine ylides with dialkyl azodicarboxylates gave the corresponding 1,2,4‐triazolidines in good yields (up to 85 %). Using chiral 8‐phenylmenthanol α‐diazo ester as the carbenoid source, chiral 1,2,4‐triazolidines have been obtained with good diastereoselectivity (up to 84 % de). Some of the 1,2,4‐triazolidines exhibited good cytotoxicity against human nasopharyngeal carcinoma (SUNE1) (IC50=10.4 μM) and human cervical carcinoma (Hela) (IC50=10.7 μM) cell lines.

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