Zinc-catalyzed cycloisomerizations. Synthesis of substituted furans and furopyrimidine nucleosides

Adam Sniady, Audrey Durham, Marco S. Morreale, Andrzej Marcinek, Slawomir Szafert, Tadeusz Lis, Krystyna R. Brzezinska, Takanori Iwasaki, Takashi Ohshima, Kazushi Mashima, Roman Dembinski

研究成果: Contribution to journalArticle査読

48 被引用数 (Scopus)

抄録

(Chemical Equation Presented) 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 μ-oxo-tetranuclear zinc cluster Zn4(OCOCF3)6O, yielded bicyclic furopyrimidine nucleosides, when starting from 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 K0bS versus In[ZnCl2 indicated first-order cycloi-somerization, as referred to ZnCl2 concentration, using both NMR and UV-vis reaction monitoring. The crystal structure of propyl furopyrimidine nucleoside (orthorhombic, P212121, a/b/c = 5.684(2)/6.682(2)/36.02(2) Å, Z = 4) shows C2′-endo deoxyribose puckering, and the base is found in the anti position in crystalline form.

本文言語英語
ページ(範囲)5881-5889
ページ数9
ジャーナルJournal of Organic Chemistry
73
15
DOI
出版ステータス出版済み - 8 1 2008
外部発表はい

All Science Journal Classification (ASJC) codes

  • 有機化学

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