期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 73, 期 15, 页码 5881-5889出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo8007995
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资金
- NCI NIH HHS [CA111329] Funding Source: Medline
5-Endo-dig cycloisomerization of 1,4- and 1,2,4- mostly aryl-substituted but-3-yn-1-ones in the presence of a catalytic amount of zinc chloride etherate (10 mol %) in dichloromethane at room temperature gave 2,5-di- and 2,3,5-trisubstituted furans in high yields (85-97%). DSC studies confirmed that a solely thermal process does not take place. A relevant catalytic process, employing mu-oxo-tetranuclear zinc cluster Zn-4(OCOCF3)(6)O, yielded bicyclic furopyrimidine nucleosides, when starting front acetyl-protected 5-alkynyl-2'-deoxyuridines (85-86%). Furopyrimidine was deprotected or simultaneously converted into pyrrolopyrimidine nucleoside. The time/concentration dependence for the reaction of 1-phenyl-4-(4-methylphenyl)butynone to 2-(4-methylphenyl)-5-phenylfuran displayed first-order kinetics with the rate dependent on catalyst concentration. The plot of In k(obs) versus In[ZnCl2] indicated first-order cycloisomerization, as referred to ZnCl2 concentration, using both NMR and UV-vis reaction monitoring The crystal structure of propyl furopyrimidine nucleoside (orthorhombic, P2(1)2(1)2(1), a/b/c = 5.684(2)/6.682(2)/36.02(2) angstrom, Z = 4) shows C2'-endo deoxyribose puckering, and the base is found in the anti position in crystalline form.
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