Synthesis of polyfluorinated ortho-alkynylanilines

An effective two-step synthesis, fluorescent properties, antioxidant activity and cytotoxicity evaluation of benzene-fluorinated 2,2-dimethyl-2,3-dihydro-1H-quinolin-4-ones

“…The reaction of 2b (255 mg, 1 mmol) and 2-methylbut-3-yn-2-ol (126 mg, 1.5 mmol), carried out according to the above general procedure, afforded the crude compound 3b (the 1 H and 19 F NMR spectra agreed with the literature data [12] The reaction of 2c (255 mg, 1 mmol) and 2-methylbut-3-yn-2-ol (126 mg, 1.5 mmol) according to the general procedure gave the crude compound 3c (the 1 H and 19 F NMR spectra agreed with the literature data [12]). PTSA (380 mg, 2 mmol) was added to the solution of crude 3c in MeOH (25 mL) and the mixture was heated under reflux for 15 h with stirring.…”

“…The combined organic layers were washed with H 2 O (40 mL) and dried (MgSO 4 ). The evaporation of the solvent in vacuo gave the crude product 3(b-f) or 4-(2-aminophenyl)-2-methylbut-3-yn-2-ol (8) that was used without further purification (the 1 H and 19 F NMR spectra agreed with the literature data [11,12]). PTSA was added to the solution of crude 3(b-f) or 8 in AlkOH (25 mL), and the mixture was heated under reflux with stirring.…”

“…PTSA (380 mg, 2 mmol) was added to the solution of crude 3c in MeOH (25 mL) and the mixture was heated under reflux for 15 h with stirring. The crude product 1c was purified by TLC (Merck precoated plates, R f 0.65 hexane/ethyl acetate, 10:1, twice) to afford the title compound (80 mg, 38%) as a C 5 ), 53.9 (s, C(CH 3 ) 2 ), 50.5 (s, CH 2 ), 27.5 (s, CH 3 ); 19 The reaction of 2d (273 mg, 1 mmol) and 2-methylbut-3-yn-2-ol (126 mg, 1.5 mmol) gave the crude compound 3d (the 1 H and 19 F NMR spectra agreed with the data reported [12] The reaction of 2e (291 mg, 1 mmol) and 2-methylbut-3-yn-2-ol (126 mg, 1.5 mmol) gave the crude compound 3e [12]. Then PTSA (190 mg, 1 mmol) was added to the solution of crude 3e in MeOH (25 mL) and the mixture was heated under reflux for 40 h with stirring.…”

“…Et 3 N, MeCN were distilled and kept over CaH 2 before to use. 2-Iodo-4,5-difluoroaniline (2b) [19], 2-iodo-4,6-difluoroaniline (2c) [12], 2-iodo-3,4,6-trifluoroaniline (2d) [12], 2-iodo-3,4,5,6-tetrafluoroaniline (2e) [12], 2-iodo-3,5,6-trifluoro-4-(trifluoromethyl)aniline (2f) [12], Pd(PPh 3 ) 2 Cl 2 [20] were prepared according to known procedures. Other starting materials were obtained from commercial supplies and used without purification.…”

“…For this purpose, we synthesized 2,2-dimethyl-2,3-dihydro-1H-quinolin-4-ones (5) via the same procedure (Scheme 1) in 90% yield based on oiodoaniline (see Section 4). [12]). …”