Advanced Research Institute and Department of Chemistry, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, P. R. China.
Department of Chemistry, Zhejiang University, Hangzhou 310058, P. R. China.
Org Lett. 2021 Dec 17;23(24):9526-9532. doi: 10.1021/acs.orglett.1c03745. Epub 2021 Dec 3.
A TfOH-promoted synthesis of fluorinated polyfused heterocycles via the cascade cyclization of azadienes and difluoroenoxysilanes has been developed, leading to the facile construction of fluorinated benzofuro[3,2-]pyridines, 5-indeno[1,2-]pyridines, and 5,6-dihydrobenzo[]quinolines. This one-pot formal [4 + 2] approach involves 1,4-difluoroalkylation, desulfonylation, cyclization, and dehydrated and dehydrofluorinated aromatization and represents the first application of difluoroenoxysilane in cascade transformations. Furthermore, this methodology is highlighted by the synthesis of three fluoro analogues of bioactive molecules with potent topoisomerase inhibitory activities.
通过氮杂二烯与二氟烯氧基硅烷的级联环化反应，开发了一种 TfOH 促进的氟化稠合杂环合成方法，可简便地构建氟化苯并[3,2-]吡啶、5-茚并[1,2-]吡啶和 5,6-二氢苯并[g]喹啉。这种一锅法的[4+2]形式反应涉及 1,4-二氟烷基化、脱磺酰基化、环化以及脱水和脱氢氟化芳构化，代表了二氟烯氧基硅烷在级联转化中的首次应用。此外，该方法学还通过合成三种具有强拓扑异构酶抑制活性的生物活性分子的氟代类似物得到了突出体现。
