Hosokawa Tsuyoshi, Matsumura Akemi, Katagiri Toshimasa, Uneyama Kenji
Department of Applied Chemistry, Faculty of Engineering, Okayama University, 3-1-1 Tsushimanaka, Okayama 700-8530, Japan.
J Org Chem. 2008 Feb 15;73(4):1468-74. doi: 10.1021/jo702568z. Epub 2008 Jan 19.
Pentafluoropropen-2-ol (PFP) was prepared by the reaction of hexafluoroacetone (HFA) with Mg/TMSCl. The one-pot tandem sequential reactions of PFP via Mannich addition with aldimines followed by Friedel-Crafts cyclization and aromatization afforded the title quinolines. A variety of corresponding 3-substituted quinolines were derived from the title quinoline by nucleophilic substitution of 3-fluorine with nucleophiles. A defluorinative transformation of the 4-trifluoromethyl group of the title quinoline with hydrazine afforded pyrazoloquinoline.
五氟丙烯 -2-醇（PFP）通过六氟丙酮（HFA）与镁/四甲基氯硅烷反应制备。PFP经曼尼希加成与醛亚胺发生一锅串联连续反应，接着进行傅克环化和芳构化反应，得到标题喹啉。通过亲核试剂对标题喹啉3-氟的亲核取代反应，可衍生出多种相应的3-取代喹啉。标题喹啉的4-三氟甲基与肼发生脱氟转化反应，得到吡唑并喹啉。
