1616862-44-2Relevant academic research and scientific papers
A combined experimental and theoretical study on the reaction mechanism and molecular structure of 4-(diphenylamino)-3-iodo-2(5H)-furanone
Song, Xiumei,Xue, Fuling,Feng, Zongcai,Wang, Yun,Wang, Zhaoyang,Xi, Yanli
, p. 837 - 844 (2017)
The simultaneous α-iodination and Nβ-arylation mechanism of 5-alkyloxy-4-phenylamino-2(5H)-furanone by (diacetoxyiodo) benzene was investigated by means of density functional theory (DFT) with B3LYP/6-31G?//LANL2DZ, selecting 4-(diphenylamino)-5-methyloxy-3-iodo-2(5H)-furanone as the calculation model. In addition, the effect of solvent on the reaction pathway was investigated using the Polarisable Continuum Model (PCM). Good agreement was found between the computational and the experimental results. Furthermore, single crystals of 4-(diphenylamino)-5-ethoxy-3-iodo-2 (5H)-furanone were grown by slow evaporation technique. The molecular structure analysis was performed by single crystal X-ray analysis and theoretical calculations using a semi-empirical quantum chemical method and DFT/B3LYP methods with a LANL2DZ as basis set.
Synthesis of 4-diarylamino-3-iodo-2(5 h)-furanones via the simultaneous α -iodination and N β-arylation by an efficient difunctionalizable transfer reagent PhI(OAc)2
Xue, Fuling,Peng, Pai,Shi, Jie,Zhong, Mingli,Wang, Zhaoyang
supporting information, p. 1944 - 1956 (2014/07/07)
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 simultaneous α-iodination and N β-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.
