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One-pot Synthesis and Characterization of 13-Acetyl-9-methyl-11-oxo-8-oxa-10,12-diazatricyclo [7.3.1.02'7] t rideca-2,4, 6-triene
Hojatollah Salehi,Qian-rong Li*,Qing-xiang Guo
Author NameAffiliation
Hojatollah Salehi Department of Chemistry,University of Science and Technology of China, Hefei 230026, China;Scholarship Department,Ministry of Science, Research and Technology, P.O. Box Tehran 15875-6186, Iran 
Qian-rong Li* Hefei National Laboratory for Physical Sciences at Microscale,Hefei 230026, China 
Qing-xiang Guo Department of Chemistry,University of Science and Technology of China, Hefei 230026, China 
Abstract:
An efficient and environmentally friendly procedure for the one-pot synthesis of 13-acetyl-9-methyl-11-oxo-8-oxa-10,12-diazatricyclo[7.3.1.02,7]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%).
Key words:  Oxygen-bridged dihydropyrimidinone, Intramolecular Michael-addition, One-pot solvent-free synthesis, NMR, EI-TOFMS
FundProject:
13-乙酰基-9-甲基-11-羰基-8-氧代-10,12-二氮杂三环[7.3.1.02,7]十三碳-2,4,6-三烯的一锅煮合成和结构表征
沙里海,李前荣*,郭庆祥
摘要:
描述了一种有效的环境友好的"一锅煮"法合成13-乙酰基-9-甲基-11-羰基-8-氧代-10,12-二氮杂三环[7.3.1.02,7]十三碳-2,4,6-三烯.该法用廉价易得的溴化镁作催化剂,在无溶剂存在下,由起始原料水杨酸,乙酰丙酮和脲通过Biginelli缩合反应伴随着分子内的Michael加成反应一步完成.用核磁共振氢谱、碳谱、飞行时间质谱以及红外光谱数据表征了产物的结构为一氧桥多环化合物,而不是带有自由羟基的二氢嘧啶酮.最后由质谱给出的精确质量及其所代表的元素组成推出了该化合物的质谱裂解途径.
关键词:  氧桥二氢嘧啶酮  分子内Michael加成  一锅煮无溶剂合成  核 磁共振  电子轰击飞行时间质谱
DOI:10.1360/cjcp2006.19(1).84.5
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