A New Method For Synthesis Of Clip Molecules Derived From Diphenylglycoluril

"Molecule clip" derive from glycoluril is an important type of host molecules. The present synthetic procedures are rather tedious. This article describes a new, simple and high effective method of synthesized this type "molecule clip".1,5-diphenylglycoluril was dissolved in a mixture of DMSO, water and KOH, then the appropriate 1,2-bischloromethylbenzene or 1,2-bisbromomethylbenzene derivative was added and stirred at room temperature. After the reaction had been completed water was added and product was filtered off, washed with water and dried under vacuum. The product purity is more than 98% even without any further purification, This constitutes the most simple procedure up to now.1,5-Diphenylglycoluril reacted with 1,2-bisbromomethylbenzene within 30min to form 4a(93%); 1,5-Diphenylglycoluril with 1,2-bischloromethylbenzene within 48h to form 4a(91%); 1,5-Diphenylglycoluril with 4,5-dimethyl-1,2-bischloromethylbenzene within 3.5h to form 4d(93%); 1,5-Diphenylglycoluril with 4,5-dimethyl-1,2-bisbromomethylbenzene within 12h to form 4d(93%); 1,5-Diphenylglycoluril with 1,2-dibromoethane within 2.5h to form 4f(80.4%); 1,5-Diphenylglycoluril with 4,5-dimethoxy-1,2-bischloromethylbenzene within 15min to form 4g(72%); 1,5-Diphenylglycoluril with 2,2'-bisbromomethyldiphenyl within 30min to form 4h(99.8%); 1,5-Diphenylglycoluril with 1,8-bischloromethylnaphthalene within 15min to form 4i(94%); 1,5-Diphenylglycoluril with 1,8-bisbromomethylnaphthalene within 15min to form 4i(97.3%); Glycoluril with 1,2-bisbromomethylbenzene within 5.5h to form 6a(68%); Glycoluril with 4,5-dimethyl-1,2-bischloromethylbenzene within 80min at 40℃to form 6b(96%); Glycoluril with 4,5-dimethoxy-1,2-bischloromethylbenzene within 30min to form 6c(38.9%).All the target clip molecules were characterized with elemental analyses, IR spectra and 1H-NMR spectra.