Department of Materials Science and Technology , Nagaoka University of Technology , 1603-1, Kamitomioka-cho, Nagaoka, Niigata 940-2188 , Japan.
J Org Chem. 2019 Sep 20;84(18):12165-12171. doi: 10.1021/acs.joc.9b01439. Epub 2019 Sep 5.
Magnesium-promoted reductive introduction of a trifluoroacetyl group to coumarin in the presence of ethyl trifluoroacetate and the subsequent treatment with trifluoroacetic acid led to simple access to a trifluoromethylated benzofurofuranone at 8a-position with a high regio- and stereoselectivity. Trifluoromethylated or difluoromethylated benzofurofuranone derivatives were also prepared from coumarins including naturally occurring ones only in two successive steps, which might have potential bioactivity in medicinal chemistry.
在三氟乙酸乙酯和三氟乙酸的存在下，镁促进的香豆素的还原引入三氟乙酰基，随后用三氟乙酸处理，导致在 8a-位以高区域和立体选择性得到简单的三氟甲基化苯并呋喃酮。仅通过两步连续反应，即可从包括天然存在的香豆素中制备出三氟甲基化或二氟甲基化苯并呋喃酮衍生物，这些衍生物在药物化学中可能具有潜在的生物活性。
