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The interesting bioactivities of 2(5H)-furanone, 1,2,3-triazole, and amino acid derivatives have promoted their combination into one multifunctional molecule. The symmetrical bis-1,2,3-triazoles and mono-1,2,3-triazoles with one free azide group are synthesized respectively by controlling the molar ratio of reactants,N-[5-alkoxy-2(5H)-furanonyl] amino acid propargyl ester and 1,4-diazidobutane. The unsymmetrical bis-1,2,3-triazoles are afforded by the subsequent reaction of mono-1,2,3-triazoles with other terminal alkynes with good to excellent yields in a short time under the same mild “click” reaction conditions. The 32 new compounds obtained in the reactions are characterized by Fourier transform infrared,1H NMR,13C NMR, mass spectrometry, and elemental analysis. Because of the diversity of four or five basic units in molecule, this methodology provides easy access to different chiral 2(5H)-furanone compounds with polyheterocyclic structure, especially with unsymmetrical bis-1,2,3-triazole moiety. Importantly, a simple approach is provided for the synthesis of unsymmetrical bis-1,2,3-triazoles using common diazides. [ABSTRACT FROM PUBLISHER]

During the studies on the intramolecular cyclization of 4-arylamino-2(5H)-furanones via the Pd-catalyzed C-H activation, a kind of difunctionalization reaction caused by the designed oxidant PhI(OAc)2[(diacetoxyiodo)benzene, DIB] was accidentally discovered. When 1.5 eq. DIB is used as a difunctionalizable transfer reagent in the 40 h reaction at 60°C and CH3CN as solvent, 4-diarylamino-3-iodo-2(5H)-furanones can be obtained with the yields of 57–91% (usually more than 73%). The simultaneousα-iodination andNβ-arylation reaction without metal catalyst is efficient and convenient. This novel utilization with a greater atom economy provides a simple and practical conversion route for the synthesis of the potential biological 2(5H)-furanone compounds containing multifunctional groups. [ABSTRACT FROM AUTHOR]

The article presents chemical equations related to Synthesis of 4-Diarylamino-3-iodo-2(5H)-furanones by an Efficient Difunctionalizable Transfer Reagent PhI(OAc)2. by P. Peng, J. SHI and others, published in the periodical "Synthetic Communications" in 2014.