Stereoselective synthesis of multifunctionalized 1,2,4-triazolidines by a ruthenium porphyrin-catalyzed three-component coupling reaction

Ming Zhong Wang, Hai Wei Xu, Yungen Liu, Man Kin Wong, Chi Ming Che

Research output: Journal article publicationJournal articleAcademic researchpeer-review

17 Citations (Scopus)

Abstract

Multifunctionalized 1,2,4-triazolidines have been synthesized by a ruthenium porphyrincatalyzed 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 (Heia) (IC50= 10.7 μM) cell lines. KGaA.
Original languageEnglish
Pages (from-to)2391-2396
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume348
Issue number16-17
DOIs
Publication statusPublished - 1 Nov 2006
Externally publishedYes

Keywords

  • 1,2,4-triazolidines
  • 1,3-dipolar cycloadditions
  • Cytotoxicity
  • Human carcinoma
  • Ruthenium porphyrins

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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