‘On water’ direct vinylogous Henry (nitroaldol) reactions of 3,5-dimethyl-4-nitroisoxazole with aldehydes and trifluoromethyl ketones

Catalytic Nucleophilic Addition of 3, 5-Dialkyl-4-nitroisoxazoles to Trifluoromethyl Ketones on Water

“…113～115 ℃ (Lit. [12] 2940,2840,1607,1525,1493,1418,1380,1365,1264,1157,1043,829,784,732 ＋ 367.0900, found 367.0903.…”

“…107～ 109 ℃ (Lit. [12] 4, 134.3, 132.1, 129.4, 128.5, 125.9, 124.6 (q, J C -F ＝284.4 Hz), 77.0 (q, J C -F ＝29.1 Hz), 33. 9, 11.4; 19 F NMR (376 MHz, CDCl 3 ) δ: -79.90 (s, 3F); IR (KBr) ν: 2923,2851,1607,1524,1450,1419,1380,1364,1266,1156,1076,1004,830,723,698 cm [12] white solid, 86% yield.…”

“…1,1,1-Trifluoro-2-(4-fluorophenyl)-3-(3-methyl-4-nitroisoxazol-5-yl)propan-2-ol (3i): [12] white solid, 99% yield. m.p.…”

“…85～86 ℃ (Lit. [12] . 2-(4-Chlorophenyl)-1,1,1-trifluoro-3-(3-methyl-4-nitroisoxazol-5-yl)propan-2-ol (3j): [12] white solid, 97% yield.…”

“…For example, in 2009, Bandini and co-workers [11] reported the guanidine-catalyzed Friedel-Crafts-type alkylation of indoles with fluoromethyl ketones in the presence of water. During the progress of our work, Zhang and Fan et al [12] reported an "on water" promoted direct vinylogous addition of 3,5-dimethyl-4-nitroisoxazole to aldehydes and trifluoromethyl ketones, but just a few examples for trifluoromethyl ketones. Recently, Michalak and co-workers [13] reported NHC-copper (I) halide-catalyzed addition of terminal alkynes with trifluoromethyl ketones on water to provide trifluoromethyl-substituted propargylic tertiary alcohols.…”