One-pot Synthesis and Characterization of 13-Acetyl-9-methyl-11-oxo-8- oxa- 10,12-d iazatricyclo [7.3.1.0^2,7] trideca- 2,4,6- triene  

作　　者：Hojatollah Salehi Qian-rong Li Qing-xiang Guo 

机构地区：[1]Hefei National Laboratory for Physical Sciences at Microscale [2]Department of Chemistry,University of Science and Technology of China, Hefei 230026, China [3]Scholarship Department,Ministry of Science, Research and Technology, P.O. Box Tehran 15875-6185, Iran

出　　处：《Chinese Journal of Chemical Physics》2006年第1期84-88,共5页化学物理学报（英文）

基　　金：This work was supported by the Natural Science Foundation of China （No.20425309）.

摘　　要：An efficient and environmentally friendly procedure for the one-pot synthesis of 13-acetyl-9-methyl-ll-oxo-8-oxa-10,12-diazatricyclo[7.3.1.0^2,7]trideca-2,4,6-triene from salicylaldehyde, acetylacetone and urea via Biginelli condensation and intramolecular Michael-addition by using magnesium bromide as an inexpensive and easily available catalyst in a solvent-free condition is described. The structural elucidation of the product is reported by ^1H- and ^13C NMR spectra. The product can also be identified by its EI TOF mass spectrometry based on the molecular ion at m/s 246（10%） and on the fragment ions in which two nitrogen atoms are remained. Three kinds of characteristic fragmentation pathways from the molecular ion were observed. One is the loss of the OH radical to form the dihydropyrimidinone cation at m/z 229（48%）, followed by elimination of a molecular methane forming the pyrimidinone cation at m/z 213（27%）. The second is the cleavage of the C6H4OH radical, and the formation of the dihydropyrimidinone cation at m/z 153（24%）. The third one is the loss of MeC-O radical to afford the oxygen-bridged fragment ion at m/z 203（33%）.

关 键 词：Oxygen-bridged dihydropyrimidinone Intramolecular Michael-addition One-pot solvent-free synthesis NMR EI-TOFMS 

分 类 号：O626.4[理学—有机化学]