Synthesis of Highly Functionalized Biaryls by Condensation of 2-Fluoro-1, 3-bis (silyloxy) 1, 3-Dienes with 3-Cyanochromones and Subsequent Domino “Retro- …

…, M Nawaz, V Wolf, A Villinger, P Langer

文献索引：Ibad, Muhammad Farooq; Abid, Obaid-Ur-Rahman; Adeel, Muhammad; Nawaz, Muhammad; Wolf, Verena; Villinger, Alexander; Langer, Peter Journal of Organic Chemistry, 2010 , vol. 75, # 23 p. 8315 - 8318

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被引用次数: 9

摘要

The Me3SiOTf-mediated condensation of 1-ethoxy-2-fluoro-1, 3-bis (trimethylsilyloxy) 1, 3- dienes with 3-cyanochromones afforded 3-cyano-2-(4-ethoxy-3-fluoro-2, 4-dioxobutyl) chroman-4-ones. Their reaction with triethylamine afforded fluorinated azaxanthones or biaryls. The product distribution depends on the structure of the diene. The formation of the biaryls can be explained by an unprecedented domino “retro-Michael/aldol/fragmentation” ...